Synthesis of Oxygenated Heterocyclic Compounds via Gold-Catalyzed Functionalization of π-Systems

  • Jose L. MascareñasEmail author
  • Fernando LópezEmail author
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 46)


During the last decade, there has been an impressive amount of new reactions catalyzed by gold (I or III) complexes, many of which lead to oxygen heterocycles in novel, practical, and efficient ways. In this chapter we have selected the most representative examples of the use of gold catalysis for the synthesis of oxygenated heterocycles, with an organization based on the type of reaction. Each section pretends to give an overview of the potential of each particular strategy and its usefulness to prepare synthetically relevant oxygenated rings. Heterocyclic systems that contain other heteroatoms in addition to oxygen have been essentially excluded, as well as those examples in which the oxygen atoms merely acts as a connecting element between two reactive functional groups.


Cyclization Cycloaddition Gold catalysis Heterocycles Organometallic catalysis Oxacycles 


  1. 1.
    Elliott MC (2000) Saturated oxygen heterocycles. J Chem Soc Perkin Trans 1:1291–1318Google Scholar
  2. 2.
    Elliot MC, Williams E (2001) J Chem Soc Perkin Trans 1 2303Google Scholar
  3. 3.
    Alali FQ, Liu XX, McLaughlin JL (1999) J Nat Prod 62:504CrossRefGoogle Scholar
  4. 4.
    Boivin TLB (1987) Tetrahedron 43:3309CrossRefGoogle Scholar
  5. 5.
    Wuitschik G, Carreira EM, Wagner B, Fischer H, Parrilla I, Schuler F, Rogers-Evans M, Müller K (2010) Oxetanes in drug discovery: structural and synthetic insights. J Med Chem 53:3227–3246CrossRefGoogle Scholar
  6. 6.
    Maes BUW, Cossy J (eds) (2014) Synthesis of saturated oxygenated heterocycles I, vol 36, Topics in heterocyclic chemistry. Springer, BerlinGoogle Scholar
  7. 7.
    Cardillo G, Orena M (1990) Stereocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediates. Tetrahedron 46:3321–3408CrossRefGoogle Scholar
  8. 8.
    Maes BUW, Cossy J (eds) (2014) Synthesis of saturated oxygenated heterocycles II, vol 36, Topics in heterocyclic chemistry. Springer, New YorkGoogle Scholar
  9. 9.
    Toste FD, Michelet V (eds) (2015) Gold catalysis: an homogeneous approach (catalytic science series). Imperial College Press, LondonGoogle Scholar
  10. 10.
    Hashmi ASK, Toste FD (eds) (2012) Modern gold catalyzed synthesis. Wiley, WeinheimGoogle Scholar
  11. 11.
    Mohr F (ed) (2009) Gold chemistry. Wiley, WeinheimGoogle Scholar
  12. 12.
    Slaughter LM (ed) (2015) Homogeneous gold catalysis, Topics in current chemistry, vol 357. Springer, ChamGoogle Scholar
  13. 13.
    Gorin DJ, Toste FD (2007) Relativistic effects in homogeneous gold catalysis. Nature 446:395–403CrossRefGoogle Scholar
  14. 14.
    Fürstner A, Davies PW (2007) Catalytic carbophilic activation: catalysis by platinum and gold pi acids. Angew Chem Int Ed 46:3410–3449CrossRefGoogle Scholar
  15. 15.
    Huguet N, Echavarren AM (2013) Gold-catalyzed O-H bond addition to unsaturated organic molecules. In: Ananikov VP, Tanaka M (eds) Hydrofunctionalization, vol 43, Topics in organometallic chemistry., pp 291–324CrossRefGoogle Scholar
  16. 16.
    Hashmi ASK, Buehrle M (2010) Gold-catalyzed addition of X-H bonds to C-C multiple bonds. Aldrichimica Acta 43:27–33Google Scholar
  17. 17.
    Corma A, Leyva-Pérez A, Sabater MJ (2011) Gold-catalyzed carbon-heteroatom bond-forming reactions. Chem Rev 111:1657–1712CrossRefGoogle Scholar
  18. 18.
    Patil NT, Kavthe RD, Shinde VS (2012) Transition metal-catalyzed addition of C-, N- and O-nucleophiles to unactivated C-C multiple bonds. Tetrahedron 68:8079–8146CrossRefGoogle Scholar
  19. 19.
    Krause N, Winter C (2011) Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles. Chem Rev 111:1994–2009CrossRefGoogle Scholar
  20. 20.
    Yang W, Hashmi ASK (2014) Mechanistic insights into the gold chemistry of allenes. Chem Soc Rev 43:2941–2955CrossRefGoogle Scholar
  21. 21.
    Hoffmann-Roder A, Krause N (2001) Gold(III) chloride catalyzed cyclization of alpha-hydroxyallenes to 2,5-dihydrofurans. Org Lett 3:2537–2538CrossRefGoogle Scholar
  22. 22.
    Winter C, Krause N (2009) Towards sustainable homogeneous gold catalysis: cycloisomerization of functionalized allenes in water. Green Chem 11:1309–1312CrossRefGoogle Scholar
  23. 23.
    Gockel B, Krause N (2006) Golden times for allenes: gold-catalyzed cycloisomerization of beta-hydroxyallenes to dihydropyrans. Org Lett 8:4485–4488CrossRefGoogle Scholar
  24. 24.
    Gockel B, Krause N (2010) Synthesis of bicyclic ethers by a gold/palladium/gold-catalyzed cyclization/cross coupling sequence. Eur J Org Chem 2010:311–316Google Scholar
  25. 25.
    Zriba R, Gandon V, Aubert C, Fensterbank L, Malacria M (2008) Alkyne versus allene activation in platinum- and gold-catalyzed cycloisomerization of hydroxylated 1,5-allenynes. Chem Eur J 14:1482–1491CrossRefGoogle Scholar
  26. 26.
    Eom D, Kang D, Lee PH (2010) Synthesis of 2-alkyl- and ary1-3-ethoxycarbony1-2,5-dihydrofurans through gold-catalyzed intramolecular hydroalkoxylation. J Org Chem 75:7447–7450CrossRefGoogle Scholar
  27. 27.
    Kim S, Lee PH (2008) Cyclization of allenyne-1,6-diols catalyzed by gold and silver salts: an efficient selective synthesis of dihydrofuran and furan derivatives. Adv Synth Catal 350:547–551CrossRefGoogle Scholar
  28. 28.
    Aksιn Ö, Krause N (2008) Gold-catalyzed synthesis of 2,5-dihydrofurans in ionic liquids. Adv Synth Catal 350:1106–1112CrossRefGoogle Scholar
  29. 29.
    Alcaide B, Almendros P, Martinez del Campo T, Fernandez I (2011) Fascinating reactivity in gold catalysis: synthesis of oxetenes through rare 4-exo-dig allene cyclization and infrequent beta-hydride elimination. Chem Commun 47:9054–9056CrossRefGoogle Scholar
  30. 30.
    Zhang ZB, Liu C, Kinder RE, Han XQ, Qian H, Widenhoefer RA (2006) Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles. J Am Chem Soc 128:9066–9073CrossRefGoogle Scholar
  31. 31.
    Alcaide B, Almendros P, del Campo TM, Soriano E, Marco-Contelles JL (2009) Regioselectivity control in the metal-catalyzed o-c functionalization of gamma-allenols, part 1: experimental study. Chem Eur J 15:1901–1908CrossRefGoogle Scholar
  32. 32.
    Alcaide B, Almendros P (2011) Gold-catalyzed heterocyclizations in alkynyl- and allenyl-beta-lactams. Beilstein J Org Chem 7:622–630CrossRefGoogle Scholar
  33. 33.
    Alcaide B, Almendros P (2014) Gold-catalyzed cyclization reactions of allenol and alkynol derivatives. Acc Chem Res 47:939–952CrossRefGoogle Scholar
  34. 34.
    Alcaide B, Almendros P, del Campo TM, Soriano E, Marco-Contelles JL (2009) Metal-catalyzed cyclization of β- and γ-allenols derived from d-glyceraldehyde-synthesis of enantiopure dihydropyrans and tetrahydrooxepines: an experimental and theoretical study. Chem Eur J 15:9127–9138CrossRefGoogle Scholar
  35. 35.
    Zhang Z, Widenhoefer RA (2007) Gold(I)-catalyzed intramolecular enantioselective hydroalkoxylation of allenes. Angew Chem Int Ed 46:283–285CrossRefGoogle Scholar
  36. 36.
    Hamilton GL, Kang EJ, Mba M, Toste FD (2007) A powerful chiral counterion strategy for asymmetric transition metal catalysis. Science 317:496–499CrossRefGoogle Scholar
  37. 37.
    Zi W, Toste FD (2015) Gold(I)-catalyzed enantioselective desymmetrization of 1,3-diols through intramolecular hydroalkoxylation of allenes. Angew Chem Int Ed. 10.1002/anie.201508331Google Scholar
  38. 38.
    Cox N, Uehling MR, Haelsig KT, Lalic G (2013) Catalytic asymmetric synthesis of cyclic ethers containing an alpha-tetrasubstituted stereocenter. Angew Chem Int Ed 52:4878–4882CrossRefGoogle Scholar
  39. 39.
    Volz F, Krause N (2007) Golden opportunities in natural product synthesis: first total synthesis of (-)-isocyclocapitelline and (-)-isochrysotricine by gold-catalyzed allene cycloisomerization. Org Biomol Chem 5:1519–1521CrossRefGoogle Scholar
  40. 40.
    Volz F, Wadman SH, Hoffmann-Roder A, Krause N (2009) Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (-)- isocyclocapitelline, and (-)-isochrysotricine. Tetrahedron 65:1902–1910CrossRefGoogle Scholar
  41. 41.
    Gao ZH, Li YF, Cooksey JP, Snaddon TN, Schunk S, Viseux EME, McAteer SM, Kocienski PJ (2009) A synthesis of an ionomycin calcium complex. Angew Chem Int Ed 48:5022–5025CrossRefGoogle Scholar
  42. 42.
    Sawama Y, Sawama Y, Krause N (2008) First total synthesis of (R, R, R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product. Org Biomol Chem 6:3573–3579CrossRefGoogle Scholar
  43. 43.
    Kang J-E, Lee E-S, Park S-I, Shin S (2005) Gold-catalyzed cyclization of tert-butyl allenoate: general synthesis of 2,4-functionalized butenolides. Tetrahedron Lett 46:7431–7433CrossRefGoogle Scholar
  44. 44.
    Liu L-P, Xu B, Mashuta MS, Hammond GB (2008) Synthesis and structural characterization of stable organogold(I) compounds. Evidence for the mechanism of gold-catalyzed cyclizations. J Am Chem Soc 130:17642–17643CrossRefGoogle Scholar
  45. 45.
    Piera J, Krumlinde P, Strübing D, Bäckvall J-E (2007) Gold-catalyzed cyclization of allene-substituted malonate esters: synthesis of β, γ-unsaturated δ-lactones. Org Lett 9:2235–2237CrossRefGoogle Scholar
  46. 46.
    Alcaide B, Almendros P, Miguel Alonso J (2011) Gold catalyzed oxycyclizations of alkynols and alkyndiols. Org Biomol Chem 9:4405–4416CrossRefGoogle Scholar
  47. 47.
    Goodwin JA, Aponick A (2015) Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes. Chem Commun 51:8730–8741CrossRefGoogle Scholar
  48. 48.
    Dorel R, Echavarren AM (2015) Gold(I)-catalyzed activation of alkynes for the construction of molecular complexity. Chem Rev 115:9028–9072CrossRefGoogle Scholar
  49. 49.
    Harkat H, Weibel JM, Pale P (2007) Synthesis of functionalized THF and THP through Au-catalyzed cyclization of acetylenic alcohols. Tetrahedron Lett 48:1439–1442CrossRefGoogle Scholar
  50. 50.
    Harkat H, Blanc A, Weibel J-M, Pale P (2008) Versatile and expeditious synthesis of aurones via aul-catalyzed cyclization. J Org Chem 73:1620–1623CrossRefGoogle Scholar
  51. 51.
    Zhdanko A, Maier ME (2015) Explanation of “silver effects” in gold(I)-catalyzed hydroalkoxylation of alkynes. ACS Catal 5:5994–6004CrossRefGoogle Scholar
  52. 52.
    Zhdanko A, Maier ME (2014) Explanation of counterion effects in gold(I)-catalyzed hydroalkoxylation of alkynes. ACS Catal 4:2770–2775CrossRefGoogle Scholar
  53. 53.
    Trost BM, Dong GB (2008) Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches. Nature 456:485–488CrossRefGoogle Scholar
  54. 54.
    Rüttinger R, Leutzow J, Wilsdorf M, Wilckens K, Czekelius C (2011) Reversal of selectivity in gold-catalyzed cyclizations of 3,3-disubstituted 1,4-diynes. Org Lett 13:224–227CrossRefGoogle Scholar
  55. 55.
    Wilckens K, Uhlemann M, Czekelius C (2009) Gold-catalyzed endo-cyclizations of 1,4-diynes to seven-membered ring heterocycles. Chem Eur J 15:13323–13326CrossRefGoogle Scholar
  56. 56.
    Murai M, Uenishi J, Uemura M (2010) Gold(I)-catalyzed asymmetric synthesis of planar chiral arene chromium complexes. Org Lett 12:4788–4791CrossRefGoogle Scholar
  57. 57.
    Hashmi ASK, Häffner T, Rudolph M, Rominger F (2011) Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)–carbene complexes. Eur J Org Chem 2011:667–671CrossRefGoogle Scholar
  58. 58.
    Kim S, Kang D, Shin S, Lee PH (2010) Gold-catalyzed cyclization of enyne-1,6-diols to substituted furans. Tetrahedron Lett 51:1899–1901CrossRefGoogle Scholar
  59. 59.
    Genin E, Toullec PY, Antoniotti S, Brancour C, Genet JP, Michelet W (2006) Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids: an entry to functionalized gamma-lactones. J Am Chem Soc 128:3112–3113CrossRefGoogle Scholar
  60. 60.
    Harkat H, Weibel JM, Pale P (2006) A mild access to gamma- or delta-alkylidene lactones through gold catalysis. Tetrahedron Lett 47:6273–6276CrossRefGoogle Scholar
  61. 61.
    Harkat H, Dembele AY, Weibel JM, Blanc A, Pale P (2009) Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between Au-I and Au-III. Tetrahedron 65:1871–1879CrossRefGoogle Scholar
  62. 62.
    Michelet V, Toullec PY, Genin E, Antoniotti S, Genet JP (2008) Au2O3 as a stable and efficient catalyst for the selective cycloisomerization of gamma-acetylenic carboxylic acids to gamma-alkylidene-gamma-butyrolactones. Synlett 707–711Google Scholar
  63. 63.
    Tomas-Mendivil E, Toullec PY, Borge J, Conejero S, Michelet V, Cadierno V (2013) Water-soluble gold(I) and gold(III) complexes with sulfonated N-heterocyclic carbene ligands: synthesis, characterization, and application in the catalytic cycloisomerization of gamma-alkynoic acids into enol-lactones. ACS Catal 3:3086–3098CrossRefGoogle Scholar
  64. 64.
    Marchal E, Uriac P, Legouin B, Toupet L, van de Weghe P (2007) Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride. Tetrahedron 63:9979–9990CrossRefGoogle Scholar
  65. 65.
    Chaladaj W, Corbet M, Fürstner A (2012) Total synthesis of neurymenolide a based on a gold-catalyzed synthesis of 4-hydroxy-2-pyrones. Angew Chem Int Ed 51:6929–6933CrossRefGoogle Scholar
  66. 66.
    Kang J-E, Shin S (2006) Au(I)-catalyzed cyclization of tert-butyl carbonates derived from ­homopropargyl alcohols: a catalytic alternative to cyclic enol carbonates. Synlett 2006:0717–0720Google Scholar
  67. 67.
    Chiarucci M, Bandini M (2013) New developments in gold-catalyzed manipulation of inactivated alkenes. Beilstein J Org Chem 9:2586–2614CrossRefGoogle Scholar
  68. 68.
    Yang C-G, He C (2005) Gold(I)-catalyzed intermolecular addition of phenols and carboxylic acids to olefins. J Am Chem Soc 127:6966–6967CrossRefGoogle Scholar
  69. 69.
    Kamiya I, Tsunoyama H, Tsukuda T, Sakurai H (2007) Lewis acid character of zero-valent gold nanoclusters under aerobic conditions: intramolecular hydroalkoxylation of alkenes. Chem Lett 36:646–647CrossRefGoogle Scholar
  70. 70.
    Chandrasekhar B, Ryu J-S (2012) Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols. Tetrahedron 68:4805–4812CrossRefGoogle Scholar
  71. 71.
    Zhang G, Cui L, Wang Y, Zhang L (2010) Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes. J Am Chem Soc 132:1474–1475CrossRefGoogle Scholar
  72. 72.
    Sahoo B, Hopkinson MN, Glorius F (2013) Combining gold and photoredox catalysis: visible light-mediated oxy- and aminoarylation of alkenes. J Am Chem Soc 135:5505–5508CrossRefGoogle Scholar
  73. 73.
    Aponick A, Li C-Y, Biannic B (2008) Au-catalyzed cyclization of monoallylic diols. Org Lett 10:669–671CrossRefGoogle Scholar
  74. 74.
    Ghebreghiorgis T, Biannic B, Kirk BH, Ess DH, Aponick A (2012) The importance of hydrogen bonding to stereoselectivity and catalyst turnover in gold-catalyzed cyclization of monoallylic diols. J Am Chem Soc 134:16307–16318CrossRefGoogle Scholar
  75. 75.
    Aponick A, Biannic B (2011) Chirality transfer in Au-catalyzed cyclization reactions of monoallylic diols: selective access to specific enantiomers based on olefin geometry. Org Lett 13:1330–1333CrossRefGoogle Scholar
  76. 76.
    Biannic B, Aponick A (2011) Gold-catalyzed dehydrative transformations of unsaturated alcohols. Eur J Org Chem 2011:6605–6617CrossRefGoogle Scholar
  77. 77.
    Aponick A, Biannic B, Jong MR (2010) A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes. Chem Commun 46:6849–6851CrossRefGoogle Scholar
  78. 78.
    Unsworth WP, Stevens K, Lamont SG, Robertson J (2011) Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone. Chem Commun 47:7659–7661CrossRefGoogle Scholar
  79. 79.
    Hashmi ASK, Schwarz L, Choi JH, Frost TM (2000) A new gold-catalyzed C-C bond formation. Angew Chem Int Ed 39:2285–2288CrossRefGoogle Scholar
  80. 80.
    Zhou CY, Chan PWH, Che CM (2006) Gold(III) porphyrin-catalyzed cycloisomerization of allenones. Org Lett 8:325–328CrossRefGoogle Scholar
  81. 81.
    Sromek AW, Rubina M, Gevorgyan V (2005) 1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans. J Am Chem Soc 127:10500–10501CrossRefGoogle Scholar
  82. 82.
    Xia YZ, Dudnik AS, Gevorgyan V, Li YH (2008) Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity. J Am Chem Soc 130:6940–6941CrossRefGoogle Scholar
  83. 83.
    Dudnik AS, Sromek AW, Rubina M, Kim JT, Kel’in AV, Gevorgyan V (2008) Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles. J Am Chem Soc 130:1440–1452CrossRefGoogle Scholar
  84. 84.
    Li Y, Brand JP, Waser J (2013) Gold-catalyzed regioselective synthesis of 2- and 3-alkynyl furans. Angew Chem Int Ed 52:6743–6747CrossRefGoogle Scholar
  85. 85.
    Belting V, Krause N (2009) Gold-catalyzed cycloisomerization of alk-4-yn-1-ones. Org Biomol Chem 7:1221–1225CrossRefGoogle Scholar
  86. 86.
    Arcadi A, Alfonsi M, Chiarini M, Marinelli F (2009) Sequential gold-catalyzed reactions of 1-phenylprop-2-yn-1-ol with 1,3-dicarbonyl compounds. J Organomet Chem 694:576–582CrossRefGoogle Scholar
  87. 87.
    Hashmi ASK, Sinha P (2004) Gold catalysis: mild conditions for the transformation of alkynyl epoxides to furans. Adv Synth Catal 346:432–438CrossRefGoogle Scholar
  88. 88.
    Blanc A, Tenbrink K, Weibel JM, Pale P (2009) Mechanistic studies and improvement of coinage metal-catalyzed transformation of alkynyloxiranes to furans: an alcohol addition-cyclization-elimination cascade. J Org Chem 74:5342–5348CrossRefGoogle Scholar
  89. 89.
    Jacques B, Hueber D, Hameury S, Braunstein P, Pale P, Blanc A, de Frémont P (2014) Synthesis, characterization, and catalytic activity of alcohol-functionalized nhc gold(i/iii) complexes. Organometallics 33:2326–2335CrossRefGoogle Scholar
  90. 90.
    Ji KG, Shu XZ, Chen J, Zhao SC, Zheng ZJ, Liu XY, Liang YM (2009) Gold-catalyzed tandem cyclization/friedel-crafts type reactions toward furan derivatives. Org Biomol Chem 7:2501–2505CrossRefGoogle Scholar
  91. 91.
    Michelet V (2015) Gold-catalyzed domino reactions. In: Slaughter LM (ed) Homogeneous gold catalysis, vol 357, Topics in current chemistry., pp 95–132Google Scholar
  92. 92.
    Inamdar SM, Konala A, Patil NT (2014) When gold meets chiral brønsted acid catalysts: extending the boundaries of enantioselective gold catalysis. Chem Commun 50:15124–15135CrossRefGoogle Scholar
  93. 93.
    Kirsch SF (2008) Construction of heterocycles by the strategic use of alkyne pi-activation in catalyzed cascade reactions. Synthesis 3183–3204Google Scholar
  94. 94.
    Zhang LM, Kozmin SA (2005) Gold-catalyzed assembly of heterobicyclic systems. J Am Chem Soc 127:6962–6963CrossRefGoogle Scholar
  95. 95.
    Toullec PY, Blarre T, Michelet V (2009) Mimicking polyolefin carbocyclization reactions: gold-catalyzed intramolecular phenoxycyclization of 1,5-enynes. Org Lett 11:2888–2891CrossRefGoogle Scholar
  96. 96.
    Sethofer SG, Mayer T, Toste FD (2010) Gold(I)-catalyzed enantioselective polycyclization reactions. J Am Chem Soc 132:8276–8277CrossRefGoogle Scholar
  97. 97.
    Fürstner A, Morency L (2008) On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions. Angew Chem Int Ed 47:5030–5033CrossRefGoogle Scholar
  98. 98.
    Sherry BD, Maus L, Laforteza BN, Toste FD (2006) Gold(I)-catalyzed synthesis of dihydropyrans. J Am Chem Soc 128:8132–8133CrossRefGoogle Scholar
  99. 99.
    Noey EL, Wang X, Houk KN (2011) Selective gold(I)-catalyzed formation of tetracyclic indolines: a single transition structure and bifurcations lead to multiple products. J Org Chem 76:3477–3483CrossRefGoogle Scholar
  100. 100.
    Cera G, Crispino P, Monari M, Bandini M (2011) Stereoselective synthesis of tetracyclic indolines via gold-catalyzed cascade cyclization reactions. Chem Commun 47:7803–7805CrossRefGoogle Scholar
  101. 101.
    Liu Y, Xu W, Wang X (2010) Gold(I)-catalyzed tandem cyclization approach to tetracyclic indolines. Org Lett 12:1448–1451CrossRefGoogle Scholar
  102. 102.
    Barluenga J, Fernández A, Satrustegui A, Dieguez A, Rodríguez F, Fañanás FJ (2008) Tandem intramolecular hydroalkoxylation-hydroarylation reactions: synthesis of enantiopure benzofused cyclic ethers from the chiral pool. Chem Eur J 14:4153–4156CrossRefGoogle Scholar
  103. 103.
    Barluenga J, Fernández A, Dieguez A, Rodríguez F, Fañanás FJ (2009) Gold- or platinum-catalyzed cascade processes of alkynol derivatives involving hydroalkoxylation reactions followed by Prins-type cyclizations. Chem Eur J 15:11660–11667CrossRefGoogle Scholar
  104. 104.
    Antoniotti S, Genin E, Michelet V, Genet JP (2005) Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols. J Am Chem Soc 127:9976–9977CrossRefGoogle Scholar
  105. 105.
    Santos LL, Ruiz VR, Sabater MJ, Corma A (2008) Regioselective transformation of alkynes into cyclic acetals and thioacetals with a gold(I) catalyst: comparison with brønsted acid catalysts. Tetrahedron 64:7902–7909CrossRefGoogle Scholar
  106. 106.
    Liu L-P, Hammond GB (2009) Highly efficient and tunable synthesis of dioxabicyclo[4.2.1] ketals and tetrahydropyrans via gold-catalyzed cycloisomerization of 2-alkynyl-1,5-diols. Org Lett 11:5090–5092CrossRefGoogle Scholar
  107. 107.
    Aponick A, Li CY, Palmes JA (2009) Au-catalyzed cyclization of monopropargylic triols: an expedient synthesis of monounsaturated spiroketals. Org Lett 11:121–124CrossRefGoogle Scholar
  108. 108.
    Paioti PHS, Ketcham JM, Aponick A (2014) Controlling regiochemistry in the gold-catalyzed synthesis of unsaturated spiroketals. Org Lett 16:5320–5323CrossRefGoogle Scholar
  109. 109.
    Minkler SR, Isley NA, Lippincott DJ, Krause N, Lipshutz BH (2014) Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature. Org Lett 16:724–726CrossRefGoogle Scholar
  110. 110.
    Liu B, De Brabander JK (2006) Metal-catalyzed regioselective oxy-functionalization of internal alkynes: an entry into ketones, acetals, and spiroketals. Org Lett 8:4907–4910CrossRefGoogle Scholar
  111. 111.
    Zhdanko A, Maier ME (2014) Gold(I)-, palladium(II)-, platinum(II)-, and Mercury(II)-catalysed spirocyclization of 1,3-enynediols: reaction scope. Eur J Org Chem 2014:3411–3422CrossRefGoogle Scholar
  112. 112.
    Jaimes MCB, Bohling CRN, Serrano-Becerra JM, Hashmi ASK (2013) Highly active mononuclear NAC-gold(I) catalysts. Angew Chem Int Ed 52:7963–7966CrossRefGoogle Scholar
  113. 113.
    Jaimes MCB, Rominger F, Pereira MM, Carrilho RMB, Carabineiro SAC, Hashmi ASK (2014) Highly active phosphite gold(I) catalysts for intramolecular hydroalkoxylation, enyne cyclization and furanyne cyclization. Chem Commun 50:4937–4940CrossRefGoogle Scholar
  114. 114.
    Quach R, Furkert DP, Brimble MA (2013) Synthesis of benzannulated spiroacetals using chiral gold-phosphine complexes and chiral anions. Tetrahedron Lett 54:5865–5868CrossRefGoogle Scholar
  115. 115.
    Yeung YY, Corey EJ (2008) A simple, efficient, and enantiocontrolled synthesis of a near-structural mimic of platensimycin. Org Lett 10:3877–3878CrossRefGoogle Scholar
  116. 116.
    Fang C, Pang YC, Forsyth CJ (2010) Formal total synthesis of okadaic acid via regiocontrolled gold(I)-catalyzed spiroketalizations. Org Lett 12:4528–4531CrossRefGoogle Scholar
  117. 117.
    Li YF, Zhou F, Forsyth CJ (2007) Gold(I)-catalyzed bis-spiroketalization: synthesis of the trioxadispiroketal-containing A-D rings of azaspiracid. Angew Chem Int Ed 46:279–282CrossRefGoogle Scholar
  118. 118.
    Liu LP, Hammond GB (2010) Gold-catalyzed cascade annulations of 2-(ynol)aryl aldehydes: facile synthesis of benzochromanes and benzobicyclo[n.3.1]acetals. Org Lett 12:4640–4643CrossRefGoogle Scholar
  119. 119.
    Tarselli MA, Zuccarello JL, Lee SJ, Gagné MR (2009) Gold(I)-catalyzed cascade cyclization of allenyl epoxides. Org Lett 11:3490–3492CrossRefGoogle Scholar
  120. 120.
    Nguyen R-V, Yao X, Li C-J (2006) Highly efficient gold-catalyzed atom-economical annulation of phenols with dienes. Org Lett 8:2397–2399CrossRefGoogle Scholar
  121. 121.
    Belting V, Krause N (2006) Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols. Org Lett 8:4489–4492CrossRefGoogle Scholar
  122. 122.
    Reddy MS, Kumar YK, Thirupathi N (2012) A new synthesis of gamma-butyrolactones via AuCl3- or Hg(II)-catalyzed intramolecular hydroalkoxylation o 4-bromo-3-yn-1ols. Org Lett 14:824–827CrossRefGoogle Scholar
  123. 123.
    Alcaide B, Almendros P, del Campo TM, Carrascosa R (2010) Metal-catalyzed cycloisomerization and tandem oxycyclization/hydroxylation of alkynols: synthesis of nonfused, spiranic and fused oxabicyclic beta-Lactams. Eur J Org Chem 2010:4912–4919Google Scholar
  124. 124.
    Diéguez-Vázquez A, Tzschucke CC, Crecente-Campo J, McGrath S, Ley SV (2009) AuCl3-Catalyzed hydroalkoxylation of conjugated alkynoates: synthesis of five- and six-membered cyclic acetals. Eur J Org Chem 2009:1698–1706Google Scholar
  125. 125.
    Hashmi ASK, Buhrle M, Wolfle M, Rudolph M, Wieteck M, Rominger F, Frey W (2010) Gold catalysis: tandem reactions of diyne-diols and external nucleophiles as an easy access to tricyclic cage-like structures. Chem Eur J 16:9846–9854CrossRefGoogle Scholar
  126. 126.
    Pennell MN, Foster RW, Turner PG, Hailes HC, Tame CJ, Sheppard TD (2014) Gold catalysed synthesis of 3-alkoxyfurans at room temperature. Chem Commun 50:1302–1304CrossRefGoogle Scholar
  127. 127.
    Alcaide B, Almendros P, Carrascosa R, Torres MR (2010) Gold/acid-cocatalyzed regiodivergent preparation of bridged ketals via direct bis-oxycyclization of alkynic acetonides. Adv Synth Catal 352:1277–1283CrossRefGoogle Scholar
  128. 128.
    Zhou L, Liu YZ, Zhang Y, Wang JB (2011) Sequential Au(I)-catalyzed reaction of water with o-acetylenyl-substituted phenyldiazoacetates. Beilstein J Org Chem 7:631–637CrossRefGoogle Scholar
  129. 129.
    Belot S, Vogt KA, Besnard C, Krause N, Alexakis A (2009) Enantioselective one-pot organocatalytic Michael addition/gold-catalyzed tandem acetalization/cyclization. Angew Chem Int Ed 48:8923–8926CrossRefGoogle Scholar
  130. 130.
    Tian GQ, Shi M (2007) Gold(I)-catalyzed additions of three-component 2-(arylmethylene)cyclopropylcarbinols, terminal arynes, and alcohols: an efficient access to 3-oxabicyclo[3.1.0]hexanes. Org Lett 9:4917–4920CrossRefGoogle Scholar
  131. 131.
    Lu BL, Dai L, Shi M (2012) Strained small rings in gold-catalyzed rapid chemical transformations. Chem Soc Rev 41:3318–3339CrossRefGoogle Scholar
  132. 132.
    Meng J, Zhao YL, Ren CQ, Li Y, Li Z, Liu Q (2009) Highly efficient access to bi- and tricyclic ketals through gold-catalyzed tandem reactions of 4-acyl-1,6-diynes. Chem Eur J 15:1830–1834CrossRefGoogle Scholar
  133. 133.
    Handa S, Slaughter LM (2012) Enantioselective alkynylbenzaldehyde cyclizations catalyzed by chiral gold(I) acyclic diaminocarbene complexes containing weak Au–arene interactions. Angew Chem Int Ed 51:2912–2915CrossRefGoogle Scholar
  134. 134.
    Wu H, He YP, Gong LZ (2013) Direct access to enantioenriched spiroacetals through asymmetric Relay catalytic three-component reaction. Org Lett 15:460–463CrossRefGoogle Scholar
  135. 135.
    Cala L, Mendoza A, Fañanás FJ, Rodríguez F (2013) A catalytic multicomponent coupling reaction for the enantioselective synthesis of spiroacetals. Chem Commun 49:2715–2717CrossRefGoogle Scholar
  136. 136.
    Jung HH, Floreancig PE (2007) Gold-catalyzed synthesis of oxygen- and nitrogen-containing heterocycles from alkynyl ethers: application to the total synthesis of andrachcinidine. J Org Chem 72:7359–7366CrossRefGoogle Scholar
  137. 137.
    Barluenga J, Calleja J, Mendoza A, Rodríguez F, Fañanás FJ (2010) Synthesis of polycyclic compounds by a cascade cycloisomerisation/Diels-Alder reaction. Chem Eur J 16:7110–7112CrossRefGoogle Scholar
  138. 138.
    Yao X, Li C-J (2006) Water-triggered and gold(I)-catalyzed cascade addition/cyclization of terminal alkynes with ortho-alkynylaryl aldehyde. Org Lett 8:1953–1955CrossRefGoogle Scholar
  139. 139.
    Hopkinson MN, Gee AD, Gouverneur V (2011) Au(I) /Au(III) catalysis: an alternative approach for C-C oxidative coupling. Chem Eur J 17:8248–8262CrossRefGoogle Scholar
  140. 140.
    Hashmi ASK, Blanco MC, Fischer D, Bats JW (2006) Gold catalysis: evidence for the in-situ reduction of gold(III) during the cyclization of allenyl carbinols. Eur J Org Chem 1387–1389Google Scholar
  141. 141.
    Wegner HA, Ahles S, Neuburger M (2008) A new gold-catalyzed domino cyclization and oxidative coupling reaction. Chem Eur J 14:11310–11313CrossRefGoogle Scholar
  142. 142.
    Zhang R, Xu Q, Chen K, Gu P, Shi M (2013) Gold-catalyzed cascade oxidative cyclization and arylation of allenoates. Eur J Org Chem 2013:7366–7371Google Scholar
  143. 143.
    Ball LT, Green M, Lloyd-Jones GC, Russell CA (2010) Arylsilanes: application to gold-catalyzed oxyarylation of alkenes. Org Lett 12:4724–4727CrossRefGoogle Scholar
  144. 144.
    Hopkinson MN, Ross JE, Giuffredi GT, Gee AD, Gouverneur V (2010) Gold-catalyzed cascade cyclization − oxidative alkynylation of allenoates. Org Lett 12:4904–4907CrossRefGoogle Scholar
  145. 145.
    Hopkinson MN, Tessier A, Salisbury A, Giuffredi GT, Combettes LE, Gee AD, Gouverneur V (2010) Gold-catalyzed intramolecular oxidative cross-coupling of nonactivated arenes. Chem Eur J 16:4739–4743CrossRefGoogle Scholar
  146. 146.
    Hashmi ASK, Lothschütz C, Döpp R, Rudolph M, Ramamurthi TD, Rominger F (2009) Gold and palladium combined for cross-coupling. Angew Chem Int Ed 48:8243–8246CrossRefGoogle Scholar
  147. 147.
    Shi Y, Roth KE, Ramgren SD, Blum SA (2009) Catalyzed catalysis using carbophilic Lewis acidic gold and Lewis basic palladium: synthesis of substituted butenolides and isocoumarins. J Am Chem Soc 131:18022–18023CrossRefGoogle Scholar
  148. 148.
    Zhang LM (2014) A non-diazo approach to alpha-oxo gold carbenes via gold-catalyzed alkyne oxidation. Acc Chem Res 47:877–888CrossRefGoogle Scholar
  149. 149.
    Ye L, Cui L, Zhang G, Zhang L (2010) Alkynes as equivalents of α-diazo ketones in generating α-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones. J Am Chem Soc 132:3258–3259CrossRefGoogle Scholar
  150. 150.
    Ye L, He W, Zhang L (2010) Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols. J Am Chem Soc 132:8550–8551CrossRefGoogle Scholar
  151. 151.
    Wang Y, Ji K, Lan S, Zhang L (2012) Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers. Angew Chem Int Ed 51:1915–1918CrossRefGoogle Scholar
  152. 152.
    Yeom H-S, Shin S (2014) Catalytic access to alpha-oxo gold carbenes by n-o bond oxidants. Acc Chem Res 47:966–977CrossRefGoogle Scholar
  153. 153.
    Shu C, Liu R, Liu S, Li J-Q, Yu Y-F, He Q, Lu X, Ye L-W (2015) Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy. Chem Asian J 10:91–95CrossRefGoogle Scholar
  154. 154.
    Wang T, Shi S, Rudolph M, Hashmi ASK (2014) Synthesis of fully substituted 3-formyl-4-iodofurans via a gold(i)-catalyzed oxidation/1,2-alkynyl migration/cyclization/iodination cascade. Adv Synth Catal 356:2337–2342CrossRefGoogle Scholar
  155. 155.
    Wang T, Huang L, Shi S, Rudolph M, Hashmi ASK (2014) Synthesis of highly substituted n-(furan-3-ylmethylene)benzenesulfonamides by a gold(i)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade. Chem Eur J 20:14868–14871CrossRefGoogle Scholar
  156. 156.
    Wang T, Shi S, Hansmann MM, Rettenmeier E, Rudolph M, Hashmi ASK (2014) Synthesis of highly substituted 3-formylfurans by a gold(I)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade. Angew Chem Int Ed 53:3715–3719CrossRefGoogle Scholar
  157. 157.
    Marion N, Nolan SP (2007) Propargylic esters in gold catalysis: access to diversity. Angew Chem Int Ed 46:2750–2752CrossRefGoogle Scholar
  158. 158.
    Correa A, Marion N, Fensterbank L, Malacria M, Nolan SP, Cavallo L (2008) Golden carousel in catalysis: the cationic gold/propargylic ester cycle. Angew Chem Int Ed 47:718–721CrossRefGoogle Scholar
  159. 159.
    Buzas A, Istrate F, Gagosz F (2006) Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans. Org Lett 8:1957–1959CrossRefGoogle Scholar
  160. 160.
    De Brabander JK, Liu B, Qian MX (2008) Au(I)- and Pt(II)-catalyzed cyclotherification of omega-hydroxy propargylic esters. Org Lett 10:2533–2536CrossRefGoogle Scholar
  161. 161.
    Wang YM, Kuzniewski CN, Rauniyar V, Hoong C, Toste FD (2011) Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters. J Am Chem Soc 133:12972–12975CrossRefGoogle Scholar
  162. 162.
    Kotikalapudi R, Swamy KCK (2013) Gold(I) catalysed cycloisomerisation of beta-hydroxy propargylic esters to dihydropyrans/2H-pyrans via allene intermediates. Tetrahedron 69:8002–8012CrossRefGoogle Scholar
  163. 163.
    Uemura M, Watson IDG, Katsukawa M, Toste FD (2009) Gold(I)-catalyzed enantioselective synthesis of benzopyrans via rearrangement of allylic oxonium intermediates. J Am Chem Soc 131:3464–3465CrossRefGoogle Scholar
  164. 164.
    Jiménez-Nuñez E, Claverie CK, Nieto-Oberhuber C, Echavarren AM (2006) Prins cyclizations in Au-catalyzed reactions of enynes. Angew Chem Int Ed 45:5452–5455CrossRefGoogle Scholar
  165. 165.
    Molawi K, Delpont N, Echavarren AM (2010) Enantioselective synthesis of (-)-englerins A and B. Angew Chem Int Ed 49:3517–3519CrossRefGoogle Scholar
  166. 166.
    Jiménez-Nuñez E, Molawi K, Echavarren AM (2009) Stereoselective gold-catalyzed cycloaddition of functionalized ketoenynes: synthesis of (+)-orientalol F. Chem Commun 7327–7329Google Scholar
  167. 167.
    Jiménez-Nuñez E, Raducan M, Lauterbach T, Molawi K, Solorio CR, Echavarren AM (2009) Evolution of propargyl ethers into allylgold cations in the cyclization of enynes. Angew Chem Int Ed 48:6152–6155CrossRefGoogle Scholar
  168. 168.
    Shu X-Z, Liu X-Y, Ji K-G, Xiao H-Q, Liang Y-M (2008) Au-catalyzed tandem cyclization/[1,2]-alkyl migration reaction of epoxyalkynes: synthesis of spiropyranones. Chem Eur J 14:5282–5289CrossRefGoogle Scholar
  169. 169.
    Lin GY, Li CW, Hung SH, Liu RS (2008) Diversity in gold- and silver-catalyzed cycloisomerization of epoxide-alkyne functionalities. Org Lett 10:5059–5062CrossRefGoogle Scholar
  170. 170.
    Lin CC, Teng TM, Tsai CC, Liao HY, Liu RS (2008) Gold-catalyzed deoxygenative Nazarov cyclization of 2,4-dien-1-als for stereoselective synthesis of highly substituted cyclopentenes. J Am Chem Soc 130:16417–16423CrossRefGoogle Scholar
  171. 171.
    Yang CY, Lin MS, Liao HH, Liu RS (2010) Diversity of products in the gold-catalyzed cyclization of 1-epoxy-1-alkynylcyclopropanes by using 1-oxyallyl cations. Chem Eur J 16:2696–2699CrossRefGoogle Scholar
  172. 172.
    Liao HH, Liu RS (2011) Effects of haloniums on gold-catalyzed ring expansion of 1-oxiranyl-1-alkynylcyclopropanes. Chem Commun 47:1339–1341CrossRefGoogle Scholar
  173. 173.
    Zhang XM, Tu YQ, Jiang YJ, Zhang YQ, Fan CA, Zhang FM (2009) Tandem reactions of cis-2-acyl-1-alkynyl-1-aryl cyclopropanes tuned by gold(I) and silver(I) catalysts: efficient synthesis of pyran-fused indene cores and 2,4,6-trisubstituted phenols. Chem Commun 4726–4728Google Scholar
  174. 174.
    Binder JT, Crone B, Kirsch SF, Liébert C, Menz H (2007) Synthesis of heterocyclic systems by transition-metal-catalyzed cyclization-migration reactions – a diversity-oriented strategy for the construction of spirocyclic 3(2H)-furanones and 3-pyrrolones. Eur J Org Chem 2007:1636–1647CrossRefGoogle Scholar
  175. 175.
    Wegener M, Huber F, Bolli C, Jenne C, Kirsch SF (2015) Silver-free activation of ligated gold(I) chlorides: the use of [Me3NB12Cl11]- as a weakly coordinating anion in homogeneous gold catalysis. Chem Eur J 21:1328–1336CrossRefGoogle Scholar
  176. 176.
    Crone B, Kirsch SF (2007) Synthesis of 4-iodo-3-furanones utilizing electrophile-induced tandem cyclization/1,2-migration reactions. J Org Chem 72:5435–5438CrossRefGoogle Scholar
  177. 177.
    Zhang J, Schmalz HG (2006) Gold(I)-catalyzed reaction of 1-(1-alkynyl)-cyclopropyl ketones with nucleophiles: a modular entry to highly substituted furans. Angew Chem Int Ed 45:6704–6707CrossRefGoogle Scholar
  178. 178.
    Fang R, Su CY, Zhao CY, Phillips DL (2009) DFT study on the mechanism and regioselectivity of gold(I)-catalyzed synthesis of highly substituted furans based on 1-(1-alkynyl)cyclopropyl ketones with nucleophiles. Organometallics 28:741–748CrossRefGoogle Scholar
  179. 179.
    Li W, Yuan W, Pindi S, Shi M, Li GG (2010) Au/Ag-catalyzed intramolecular ring-opening of vinylidene-cyclopropanes (VDCPs): an easy Access to functional tetrahydropyrans. Org Lett 12:920–923CrossRefGoogle Scholar
  180. 180.
    Peng B, Maulide N (2013) The redox-neutral approach to C-H functionalization. Chem Eur J 19:13274–13287CrossRefGoogle Scholar
  181. 181.
    Jurberg ID, Odabachian Y, Gagosz F (2010) Hydroalkylation of alkynyl ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence. J Am Chem Soc 132:3543–3552CrossRefGoogle Scholar
  182. 182.
    Vadola PA, Sames D (2009) C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide. J Am Chem Soc 131:16525–16528CrossRefGoogle Scholar
  183. 183.
    Bolte B, Gagosz F (2011) Gold and brønsted acid catalyzed hydride shift onto allenes: divergence in product selectivity. J Am Chem Soc 133:7696–7699CrossRefGoogle Scholar
  184. 184.
    López F, Mascareñas JL (2011) Recent developments in gold-catalyzed cycloaddition reactions. Beilstein J Org Chem 7:1075–1094CrossRefGoogle Scholar
  185. 185.
    López F, Mascareñas JL (2013) Gold(I)-catalyzed enantioselective cycloaddition reactions. Beilstein J Org Chem 9:2250–2264CrossRefGoogle Scholar
  186. 186.
    Garayalde D, Nevado C (2012) Gold-containing and gold-generated 1, n-dipoles as useful platforms toward cycloadditions and cyclizations. ACS Catal 2:1462–1479CrossRefGoogle Scholar
  187. 187.
    Teng TM, Das A, Huple DB, Liu RS (2010) Gold-catalyzed stereoselective synthesis of 9-oxabicyclo[3.3.1]nona-4,7-dienes from diverse 1-oxo-4-oxy-5-ynes: a viable formal [4 + 2] cycloaddition on an s-trans-heterodiene framework. J Am Chem Soc 132:12565–12567CrossRefGoogle Scholar
  188. 188.
    Teng TM, Liu RS (2010) Gold-catalyzed stereocontrolled oxacyclization/[4 + 2]-cycloaddition cascade of ketone-allene substrates. J Am Chem Soc 132:9298–9300CrossRefGoogle Scholar
  189. 189.
    Zhang G, Zhang L (2008) Au-containing all-carbon 1,3-dipoles: generation and [3 + 2] cycloaddition reactions. J Am Chem Soc 130:12598–12599CrossRefGoogle Scholar
  190. 190.
    Gao H, Wu X, Zhang J (2010) Exo/endo selectivity-control in Lewis-acid catalyzed tandem heterocyclization/formal [4 + 3] cycloaddition: synthesis of polyheterocycles from 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran. Chem Commun 46:8764–8766CrossRefGoogle Scholar
  191. 191.
    Zhang G, Huang X, Li G, Zhang L (2008) Au-containing all-carbon 1,4-dipoles: generation and [4 + 2] annulation in the formation of carbo-/heterocycles. J Am Chem Soc 130:1814–1815CrossRefGoogle Scholar
  192. 192.
    Escribano-Cuesta A, Lopez-Carrillo V, Janssen D, Echavarren AM (2009) Gold-catalyzed reactions of 1,5-and 1,6-enynes with carbonyl compounds: cycloaddition vs. metathesis. Chem Eur J 15:5646–5650CrossRefGoogle Scholar
  193. 193.
    Schelwies M, Dempwolff AL, Rominger F, Helmchen G (2007) Gold-catalyzed intermolecular addition of carbonyl compounds to 1,6-enynes. Angew Chem Int Ed 46:5598–5601CrossRefGoogle Scholar
  194. 194.
    Zhou Q, Chen X, Ma D (2010) Asymmetric, protecting-group-free total synthesis of (-)-englerin A. Angew Chem Int Ed 49:3513–3516CrossRefGoogle Scholar
  195. 195.
    Obradors C, Echavarren AM (2013) Intermolecular gold-catalyzed cycloaddition of alkynes with oxoalkenes. Chem Eur J 19:3547–3551CrossRefGoogle Scholar
  196. 196.
    Faustino H, Alonso I, Mascareñas JL, López F (2013) Gold(I)-catalyzed cascade cycloadditions between allenamides and carbonyl-tethered alkenes: an enantioselective approach to oxa-bridged medium-sized carbocycles. Angew Chem Int Ed 52:6526–6530CrossRefGoogle Scholar
  197. 197.
    Faustino H, Varela I, Mascareñas JL, López F (2015) Gold(I)-catalyzed 2 + 2 + 2 cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans. Chem Sci 6:2903–2908CrossRefGoogle Scholar
  198. 198.
    Li CW, Lin GY, Liu RS (2010) Construction of 2,3-dihydrofuran cores through the [3 + 2] cycloaddition of gold alpha-carbonylcarbenoids with alkenes. Chem Eur J 16:5803–5811CrossRefGoogle Scholar
  199. 199.
    Teng TM, Lin MS, Vasu D, Bhunia S, Liu TA, Liu RS (2010) Gold-catalyzed dealkoxylative carbocyclization/[3 + 3] annulation cascade of acetal-allene or ketal-allene substrates. Chem Eur J 16:4744–4748CrossRefGoogle Scholar
  200. 200.
    Kramer S, Skrydstrup T (2012) Gold-catalyzed carbene transfer to alkynes: access to 2,4-disubstituted furans. Angew Chem Int Ed 51:4681–4684CrossRefGoogle Scholar
  201. 201.
    Huang XL, Peng B, Luparia M, Gomes LFR, Veiros LF, Maulide N (2012) Gold-catalyzed synthesis of furans and furanones from sulfur ylides. Angew Chem Int Ed 51:8886–8890CrossRefGoogle Scholar
  202. 202.
    Yeom H-S, Koo J, Park H-S, Wang Y, Liang Y, Yu Z-X, Shin S (2012) Gold-catalyzed intermolecular reactions of propiolic acids with alkenes: 4 + 2 annulation and enyne cross metathesis. J Am Chem Soc 134:208–211CrossRefGoogle Scholar
  203. 203.
    Trillo B, López F, Montserrat S, Ujaque G, Castedo L, Lledós A, Mascareñas JL (2009) Gold-catalyzed [4C + 3C] intramolecular cycloaddition of allenedienes: synthetic potential and mechanistic implications. Chem Eur J 15:3336–3339CrossRefGoogle Scholar
  204. 204.
    Gung BW, Craft DT (2009) Gold-catalyzed transannular [4 + 3] cycloaddition reactions. Tetrahedron Lett 50:2685–2687CrossRefGoogle Scholar
  205. 205.
    Gung BW, Craft DT, Bailey LN, Kirschbaum K (2010) Gold-catalyzed transannular [4 + 3] cycloaddition reactions. Chem Eur J 16:639–644CrossRefGoogle Scholar
  206. 206.
    Yang JM, Tang XY, Shi M (2015) Gold(I)-catalyzed intramolecular cycloisomerization of propargylic esters with furan rings. Chem Eur J 21:4534–4540CrossRefGoogle Scholar
  207. 207.
    Alonso I, Trillo B, López F, Montserrat S, Ujaque G, Castedo L, Lledós A, Mascareñas JL (2009) Gold-catalyzed 4C + 2C cycloadditions of allenedienes, including an enantioselective version with New phosphoramidite-based catalysts: mechanistic aspects of the divergence between 4c + 3c and 4c + 2c pathways. J Am Chem Soc 131:13020–13030CrossRefGoogle Scholar
  208. 208.
    Mauleón P, Zeldin RM, González AZ, Toste FD (2009) Ligand-controlled access to [4 + 2] and [4 + 3] cycloadditions in gold-catalyzed reactions of allene-dienes. J Am Chem Soc 131:6348–6349CrossRefGoogle Scholar

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© Springer International Publishing Switzerland 2016

Authors and Affiliations

  1. 1.Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química OrgánicaUniversidad de Santiago de CompostelaSantiago de CompostelaSpain
  2. 2.Instituto de Química Orgánica General (CSIC)MadridSpain

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