Advertisement

Organocatalyzed Cycloadditions

Chapter

Abstract

Cycloadditions have been for a long time one of the most useful reactions in organic synthesis. Recently, the ability to promote the reactions by organocatalysts further expands the realm of its synthetic application. This review aims to highlight the recent advances in this area with particular emphasis on the asymmetric cycloaddition promoted by organocatalysts.

Keywords

Cycloaddition Reaction Alder Reaction Cinchona Alkaloid Azomethine Ylides Ethyl Vinyl Ether 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    For a review and discussion in the organocatalysis lost, see: (a) MacMillan DWC (2008) Nature 455:304; (b) Barbas CF III (2008) Angew Chem Int Edit 47:42Google Scholar
  2. 2.
    For recent reviews in organocatalysis, see: (a) Palomo C, Oiarbide M, López R (2009) Chem Soc Rev 38:632; (b) Zhang Z, Schreiner PR (2009) Chem Soc Rev 38:1187; (c) Bella M, Gasperi T (2009) Synthesis 1583; (d) Lattanzi A (2009) Chem Commun 1452; (e) Ueda M, Kano T, Maruoka K (2009) Org Biomol Chem 7:2005; (f) Dohi T, Kita Y (2009) Chem Commun 2073; (g) Gruttadauria M, Giacalone F, Noto R (2009) Adv Synth Cat 351:33; (h) Xu LW, Luo J, Lu Y (2009) Chem Commun 1807; (i) Melchiorre P (2009) Angew Chem Int Edit 48:1360; (j) Toma S, Meciarova M, Sebesta R (2009) Eur J Org Chem 321; (k) Connon SJ (2009) Synlett 354; (l) MacMillan DWC (2008) Nature 455:304; (m) Carlos FB III (2008) Angew Chem Int Edit 47:42; (n) Dondoni A, Massi A (2008) Angew Chem Int Edit 47:4638; (o) Poisson T (2008) Synlett 147; (p) Melchiorre P, Marigo M, Carlone A, Bartoli G (2008) Angew Chem Int Edit 47:6138; (q) Mielgo A, Palomo C (2008) Asian J Chem 3:922; (r) Yu X, Wang W (2008) Org Biomol Chem 6:2037; (s) Longbottom DA, Franckevicius V, Kumarn S, Oelke AJ, Wascholowski V, Ley SV (2008) Aldrichim Acta 41:3; (t) Seebach D, Groselj U, Badine DM, Schweizer WB, Beck AK (2008) Helv Chim Acta 91:1999; (u) Kano T, Maruoka K (2008) Chem Commun 5465; (v) Renaud P, Leong P (2008) Science 322:55; (w) Peng F, Shao Z (2008) J Mol Catal A-Chem 285:1; (x) Dominguez de Maria P (2008) Angew Chem Int Edit 47:6960; (y) Enders D, Narine AA (2008) J Org Chem 73:7857; (z) Duschek A, Kirsch SF (2008) Angew Chem Int Edit 47:5703; (aa) Bartoli G, Melchiorre P (2008) Synlett 1759; (ab) Yu X, Wang W (2008) Asian J Chem 3:516; (ac) Wong OA, Shi Y (2008) Chem Rev 108:3958; (ad) Alcaide B, Almendros P (2008) Angew Chem Int Edit 47:4632; (ae) Chen YC (2008) Synlett 1919; (af) Gruttadauria M, Giacalone F, Noto R (2008) Chem Soc Rev 37:1666; (ag) Kocovsky P, Malkov AV (2008) Pure Appl Chem 80:953; (ah) Xu LW, Lu Y (2008) Org Biol Chem 6:2047; (ai) Connon SJ (2008) Chem Commun 2499; (aj) Markert M, Mahrwald R (2008) Chem Eur J 14:40; (ak) Seki M (2008) Synlett 164; (al) Verkade JMM, van Hemert LJC, Quaedflieg PJLM, Rutjes FPJT (2008) Chem Soc Rev 37:29; (am) List B (ed) (2007) Thematic issues: (12) Chem Rev 107:5413; (an) de Figueiredo RM, Christmann M (2007) Eur J Org Chem 2575; (ao) Gaunt MJ, Johansson CCC, McNally A, Vo NC (2007) Drug Discov Today 12:8; (ap) Ikunaka M (2007) Org Process Res Dev 11:495; (aq) Dalko PI (ed) (2007) Enantioselective organocatalysis: reactions and experimental procedures. Willey-VCH, Weinheim; (ar) Enders D, Grondal C, Hüttl MRM (2007) Angew Chem Int Edit 46:1570; (as) Christmann M, Braese S (eds) (2007) Asymmetric synthesis: the essentials. Wiley-VCH, Weinheim; (at) Kellogg RM (2007) Angew Chem Int Edit 46:494; (au) Walji AM, MacMillan DWC (2007) Synlett 1477; (av) Guillena G, Nájera C, Ramón DJ (2007) Tetrahedron-Asymmetr 18:2249; (aw) Pellissier H (2007) Tetrahedron 63:9267; (ax) Sulzer-Mossé S, Alexandre A (2007) Chem Commun 3123; (ay) Vicario JL, Badía D, Carrillo L (2007) Synthesis 2065; (az) Guillena G, Ramón DJ, Yus M (2007) Tetrahedron-Asymmetr 18:693; (ba) Chapman CJ, Frost CG (2007) Synthesis 1; (bb) Almasi D, Alonso DA, Nájera C (2007) Tetrahedron-Asymmetr 18:299; (bc) Tietze LF, Brasche G, Gericke K (2007) Domino reactions in organic synthesis. Wiley-VCH, Weinheim; (bd) Ting A, Schaus SE (2007) Eur J Org Chem 5797; (be) Brehme R, Enders D, Fernandez R, Lassaletta JM (2007) Eur J Org Chem 5629; (bf) McGarrigle EM, Myers EL, Illa O, Shaw MA, Riches SL, Aggarwal VK (2007) Chem Rev 107:5841; (bg) Gong LZ, Chen XH, Xu XY (2007) Chem Eur J 13:8920; (bh) Kamber NE, Jeong W, Waymouth RM, Pratt RC, Lohmeijer BGG, Hedrick JL (2007) Chem Rev 107:5813; (bi) Boysen MMK (2007) Chem Eur J 13:8648; (bj) Bertelsen S, Nielsen M, Jørgensen KA (2007) Angew Chem Int Edit 46:7356; (bk) Connon SJ (2007) Org Biomol Chem 5:3407; (bl) Enders D, Niemeier O, Henseler A (2007) Chem Rev 107:5606; (bm) Jaroch S, Weinmann H, Zeitler K (2007) Chem Med Chem 2:1261; (bn) Pellissier H (2007) Tetrahedron 63:9267; (bo) Palomo C, Oiarbide M, Laso A (2007) Eur J Org Chem 2561; (bp)You SL (2007) Asian J Chem 2:820; (bq) Marion N, Diez-Gonzalez S, Nolan SP (2007) Angew Chem Int Edit 46:2988; (br) Tsogoeva SB (2007) Eur J Org Chem 11:1701; (bs) Lelais G, MacMillan DWC (2007) New Front Asym Catal 313; (bt) Guino M, Hii KK (2007) Chem Soc Rev 36: 608; (bu) Maruoka K, Ooi T, Kano T (2007) Chem Commun 15:1487; (bv) Ley SV (2007) In: Christmann M, Bräse S (eds) Asymmetric Synthesis: The Essentials, 2nd, Completely Revised Edition Wiley-VCH, Weinheim, p 211; (bw) List B (2007) In: Christmann M, Bräse S (eds) Asymmetric Synthesis: The Essentials, 2nd, Completely Revised Edition Wiley-VCH, Weinheim, p 169; (bx) Jørgensen KA (2007) In: Christmann M, Bräse S (eds) Asymmetric Synthesis: The Essentials, 2nd, Completely Revised Edition Wiley-VCH, Weinheim, p 200; (by) Brogan AP, Dickerson TJ, Janda KD (2006) Angew Chem Int Edit 45:8100; (bz) Marigo M, Jørgensen KA (2006) Chem Commun 2001; (ca) List B (2006) Chem Comm 8:819; (cb) Marcelli T, van Maarseveen JH, Hiemstra H (2006) Angew Chem Int Edit 45:7496; (cc) Akiyama T, Itoh J, Fuchibe K (2006) Adv Synth Catal 348:999; (cd) Yamamoto H, Doyle MP (eds) (2006) Catalytic cycloaddition reactions (Special issue) Adv Synth Catal 348:2253; (ce) Wasilke JC, Obrey SJ, Baker RT, Bazan GC (2005) Chem Rev 105:1001; (cf) Tejedor D, González-Cruz D, Santos-Expósito A, Marrero-Tellado JJ, Armas P, García-Tellado F (2005) Chem Eur J 11:3502; (cg) List B, Bolm C (eds) (2004) Organic catalysis (Special issue) Adv Synth Catal 346:1007; (ch) Alba AN, Companyo X, Viciano M, Rios R (2009) Curr Org Chem 13:1432; (ci) Raja M, Singh VK (2009) Chem Commun 6687; (cj) Bertelsen S, Jørgensen KA (2009) Chem Soc Rev 38:2178; (ck) Enders D, Wang C, Liebich JX (2009) Chem Eur J 15:11058; (cl) Erkkila A, Majander I, Pihko PM (2007) Chem Rev 107:5416Google Scholar
  3. 3.
    Houk KN, Cheong PHY (2008) Nature 455:309CrossRefGoogle Scholar
  4. 4.
    (a) Ess DH, Jones GO, Houk KN (2006) Adv Synth Catal 348:2337; (b) Gordillo R, Houk KN (2006) J Am Chem Soc 128:3543 (c) Seebach D, Gilmour R, Grošelj U, Deniau G, Sparr C, Ebertm MO, Beck AK, McCusker LB, Šišak D, Uchimaru T (2010) Helv Chim Acta 93:603Google Scholar
  5. 5.
    Wilson RM, Jen WS, MacMillan DWC (2005) J Am Chem Soc 127:11616CrossRefGoogle Scholar
  6. 6.
    (a) Lambert TH, Danishefsky SJ (2006) J Am Chem Soc 128:426; (b) Figueiredo RM, Fröhlich R, Christmann M (2007) Angew Chem Int Edit 46:2883Google Scholar
  7. 7.
    (a) Figueiredo RM, Voith M, Fröhlich R, Christmann M (2007) Synlett 391; (b) Christmann M (2007) In: Ernst Schering foundation symposium proceedings 2:125Google Scholar
  8. 8.
    Figueiredo RM, Fröhlich R, Christmann M (2008) Angew Chem Int Edit 47:1450CrossRefGoogle Scholar
  9. 9.
    The electron-rich dienamine has been observed by NMR, see: Bertelsen S, Marigo M, Brandes S, Diner P, Jørgensen KA (2006) J Am Chem Soc 128:12973Google Scholar
  10. 10.
    Jacobs WC, Christmann M (2008) Synlett 39:247Google Scholar
  11. 11.
    Selkälä SA, Koskinen AMP (2005) Eur J Org Chem 9:1620CrossRefGoogle Scholar
  12. 12.
    (a) Wang JC, Krische MJ (2003) Angew Chem Int Edit 42:5855 (b) Wang JC, Ng SS, Krische MJ (2003) J Am Chem Soc 125:3682Google Scholar
  13. 13.
    Muller C, Bauer A, Bach T (2009) Angew Chem Int Edit 48:6640CrossRefGoogle Scholar
  14. 14.
    (a) Lelais G, MacMillan DWC (2006) Aldrichimica Acta 39:79 (b) Erkkila A, Majander I, Pihko PM (2007) Chem Rev 107:5416 (c) Merino P, Marqués-López E, Tejero T, Herrera RP (2010) Synthesis 1Google Scholar
  15. 15.
    Shen J, Tan CH (2007) Org Biomol Chem 6:3229CrossRefGoogle Scholar
  16. 16.
    Langlois Y, Kouklovsky C (2009) Synlett 3065CrossRefGoogle Scholar
  17. 17.
    Gioia C, Bernardi L, Ricci A (2010) Synthesis 161Google Scholar
  18. 18.
    For other reviews: Wang C, Liu WH, Zhou X (2009) Progress Chem 21:1857Google Scholar
  19. 19.
    Ahrendt KA, Borths CJ, MacMillan DWC (2000) J Am Chem Soc 122:4243CrossRefGoogle Scholar
  20. 20.
    Northrup AB, MacMillan DWC (2002) J Am Chem Soc 124:2458CrossRefGoogle Scholar
  21. 21.
    Dumm TB, Ellis JM, Kofink CC, Manning JR, Overman LE (2009) Org Lett 11:5658CrossRefGoogle Scholar
  22. 22.
    Gotoh H, Hayashi Y (2007) Org Lett 9:2859CrossRefGoogle Scholar
  23. 23.
    Hayashi Y, Samanta S, Gotoh H, Ishikawa H (2008) Angew Chem Int Edit 47:6634CrossRefGoogle Scholar
  24. 24.
    Evans G, Gibbs TJK, Jenkins RL, Coles SJ, Hursthouse MB, Platts JA, Tomkinson NCO (2008) Angew Chem Int Edit 47:2820CrossRefGoogle Scholar
  25. 25.
    (a) Lemay M, Aumand L, Ogilvie WW (2007) Adv Synth Catal 349:441 (b) Lemay M, Ogilvie WW, (2005) Org Lett 7:4141 (c) Lemay M, Ogilvie WW (2006) J Org Chem 71:4663Google Scholar
  26. 26.
    Kim KH, Lee S, Lee DW, Ko DH, Ha DC (2005) Tetrahedron Lett 46:5991CrossRefGoogle Scholar
  27. 27.
    (a) Kano T, Tanaka Y, Maruoka K (2006) Org Lett 8:2687 (b) Kano T, Tanaka Y, Maruoka K (2007) Asian J Chem 2:1161Google Scholar
  28. 28.
    Zhang Y, Zhao L, Lee SS, Ying JY (2006) Adv Synth Catal 348:2027CrossRefGoogle Scholar
  29. 29.
    Kano T, Tanaka Y, Osawa K, Yurino T, Maruoka K (2009) Chem Comm 15:1956CrossRefGoogle Scholar
  30. 30.
    Ma Y, Zhang YJ, Jin S, Li Q, Li C, Lee J, Zhang W (2009) Tetrahedron Lett 50:7388CrossRefGoogle Scholar
  31. 31.
    Braddock DC, MacGilp ID, Perry BG (2003) Synlett 8:1121CrossRefGoogle Scholar
  32. 32.
    Hartikka A, Hojabri L, Bose PP, Arvidsson PI (2009) Tetrahedron: Asymmetr 20:1871CrossRefGoogle Scholar
  33. 33.
    Bonini BF, Capitò E, Comes-Franchini M, Fochi M, Ricci A, Zwanenburg B (2006) Tetrahedron: Asymmetr 17:3135CrossRefGoogle Scholar
  34. 34.
    He H, Pei BJ, Chou HH, Tian T, Lee AWM (2008) Org Lett 10:2421CrossRefGoogle Scholar
  35. 35.
    Langlois Y, Petit A, Remy P, Scherrmann MC, Kouklovsky C (2008) Tetrahedron Lett 49:5576CrossRefGoogle Scholar
  36. 36.
    Selkälä SA, Tois J, Pihko PM, Koskinen AMP (2002) Adv Synth Catal 344:941CrossRefGoogle Scholar
  37. 37.
    (a) Wang Y, Li H, Wang YQ, Liu Y, Foxman BM, Deng L (2007) J Am Chem Soc 129:6364 (b) Singh RP, Bartelson K, Wang Y, Su H, Lu X, Deng L (2008) J Am Chem Soc 130:2422Google Scholar
  38. 38.
    Xu DQ, Xia AB, Luo SP, Tang J, Zhang S, Jiang JR, Xu ZY (2009) Angew Chem Int Edit 48:3821CrossRefGoogle Scholar
  39. 39.
    Bekele T, Shah MH, Wolfer J, Abraham CJ, Weatherwax A, Lectka T (2006) J Am Chem Soc 128:1810CrossRefGoogle Scholar
  40. 40.
    Wolfer J, Bekele T, Abraham CJ, Dogo-Isonagie C, Lectka T (2006) Angew Chem Int Edit 45:7398CrossRefGoogle Scholar
  41. 41.
    Juhl K, Jørgensen KA (2003) Angew Chem Int Edit 42:1498CrossRefGoogle Scholar
  42. 42.
    Tiseni PS, Peters R (2007) Angew Chem Int Edit 46:5325CrossRefGoogle Scholar
  43. 43.
    He M, Struble JR, Bode JW (2006) J Am Chem Soc 128:8418CrossRefGoogle Scholar
  44. 44.
    He M, Uc GJ, Bode JW (2006) J Am Chem Soc 128:15088CrossRefGoogle Scholar
  45. 45.
    He M, Beahm BJ, Bode JW (2008) Org Lett 10:3817CrossRefGoogle Scholar
  46. 46.
    Han B, Li JL, Ma C, Zhang SJ, Chen YC (2008) Angew Chem Int Edit 47:9971CrossRefGoogle Scholar
  47. 47.
    He ZQ, Han B, Li R, Wu L, Chen YC (2010) Org Biomol Chem 8:755CrossRefGoogle Scholar
  48. 48.
    Han B, He ZQ, Li JL, Li R, Jiang K, Liu TY, Chen YC (2009) Angew Chem Int Edit 48:5474CrossRefGoogle Scholar
  49. 49.
    Itoh J, Fuchibe K, Akiyama T (2006) Angew Chem Int Edit 45:4796CrossRefGoogle Scholar
  50. 50.
    Aznar F, García AB, Cabal MP (2006) Adv Synth Catal 348:2443CrossRefGoogle Scholar
  51. 51.
    (a) Bergonzini G, Gramigna L, Mazzanti A, Fochi M, Bernardi L, Ricci A (2010) Chem Commun 46:327 (b) Gioia C, Hauville A, Bernardi L, Fini F, Ricci A (2008) Angew Chem Int Edit 47:9236Google Scholar
  52. 52.
    Zhang X, Du H, Wang Z, Wu YD, Ding K (2006) J Org Chem 71:2862CrossRefGoogle Scholar
  53. 53.
    Kobayashi S, Kinoshita T, Uehara H, Sudo T, Ryu I (2009) Org Lett 11:3934CrossRefGoogle Scholar
  54. 54.
    Sundén H, Ibrahem I, Eriksson L, Córdova A (2005) Angew Chem Int Edit 44:4877CrossRefGoogle Scholar
  55. 55.
    Rueping M, Azap C (2006) Angew Chem Int Edit 45:7832CrossRefGoogle Scholar
  56. 56.
    Liu H, Cun LF, Mi AQ, Jiang YZ, Gong LZ (2006) Org Lett 8:6023CrossRefGoogle Scholar
  57. 57.
    Terzidis MA, Dimitriadou E, Tsoleridis CA, Stephanidou-Stephanatou J (2009) Tetrahedron Lett 50:2174CrossRefGoogle Scholar
  58. 58.
    Jones SB, Simmons B, MacMillan DWC (2009) J Am Chem Soc 131:13606CrossRefGoogle Scholar
  59. 59.
    Ishihara K, Nakano K, Akakura M (2008) Org Lett 10:2893CrossRefGoogle Scholar
  60. 60.
    (a) Sakakura A, Suzuki K, Ishihara K (2006) Adv Synth Catal 348:2457; (b) Sakakura A, Suzuki K, Nakano K, Ishihara K (2006) Org Lett 8:2229; (c) Ishihara K, Nakano K (2005) J Am Chem Soc 127:10504, 13079 (additions and corrections)Google Scholar
  61. 61.
    Akalay D, Dürner G, Göbel MW (2008) Eur J Org Chem 14:2365CrossRefGoogle Scholar
  62. 62.
    Xie H, Zu L, Oueis HR, Li H, Wang J, Wang W (2008) Org Lett 10:1923CrossRefGoogle Scholar
  63. 63.
    Xu X, Wang K, Nelson SG (2007) J Am Chem Soc 129:11690CrossRefGoogle Scholar
  64. 64.
    Lv H, You L, Ye S (2009) Adv Synth Catal 351:2822CrossRefGoogle Scholar
  65. 65.
    Huang XL, He L, Shao PL, Ye S (2009) Angew Chem Int Edit 48:192Google Scholar
  66. 66.
    Hayashi Y, Gotoh H, Masui R, Ishikawa H (2008) Angew Chem Int Edit 47:4012CrossRefGoogle Scholar
  67. 67.
    Zu L, Xie H, Li H, Wang J, Yu X, Wang W (2008) Chem Eur J 14:6333CrossRefGoogle Scholar
  68. 68.
    Ishihara K, Nakano K (2007) J Am Chem Soc 129:8930CrossRefGoogle Scholar
  69. 69.
    (a) Zhu C, Shen X, Nelson SG (2004) J Am Chem Soc 126:5352; (b) Shen X, Wasmuth AS, Zhao J, Zhu C, Nelson SG (2006) J Am Chem Soc 128:7438Google Scholar
  70. 70.
    Armstrong A, Geldart SP, Jenner CR, Scutt JN (2007) J Org Chem 72:8091CrossRefGoogle Scholar
  71. 71.
    Sereda O, Blanrue A, Wilhelm R (2009) Chem Commun 40:1040CrossRefGoogle Scholar
  72. 72.
    Zajac M, Peters R (2009) Chem Eur J 15:8204CrossRefGoogle Scholar
  73. 73.
    Jiang JL, Ju J, Hua R (2007) Org Biomol Chem 5:1854CrossRefGoogle Scholar
  74. 74.
    Harmata M, Ghosh SK, Hong X, Wacharasindhu S, Kirchhoefer P (2003) J Am Chem Soc 125:2058CrossRefGoogle Scholar
  75. 75.
    Jen WS, Wiener JJ, MacMillan DWC (2000) J Am Chem Soc 122:9874CrossRefGoogle Scholar
  76. 76.
    Karlsson S, Hogberg HE (2002) Tetrahedron: Asymmetr 13:923CrossRefGoogle Scholar
  77. 77.
    Chow SS, Nevalainen M, Evans CA, Johannes CW (2007) Tetrahedron Lett 48:277CrossRefGoogle Scholar
  78. 78.
    Ibrahem I, Rios R, Vesely J, Zhao GL, Córdova A (2007) Chem Comm 8:849CrossRefGoogle Scholar
  79. 79.
    Weselinski L, Stepniak P, Jurczak J (2009) Synlett 14:2261Google Scholar
  80. 80.
    Jiao P, Nakashima D, Yamamoto H (2008) Angew Chem Int Edit 47:2411CrossRefGoogle Scholar
  81. 81.
    Gioia C, Fini F, Mazzanti A, Bernardi L, Ricci A (2009) J Am Chem Soc 131:9614CrossRefGoogle Scholar
  82. 82.
    Vicario JL, Reboredo S, Badia D, Carrillo L (2007) Angew Chem Int Edit 46:5168CrossRefGoogle Scholar
  83. 83.
    Ibrahem I, Rios R, Vesely J, Córdova A (2007) Tetrahedron Lett 48:6252CrossRefGoogle Scholar
  84. 84.
    Rios R, Ibrahem I, Vesely J, Sundén H, Córdova A (2007) Tetrahedron Lett 48:8695CrossRefGoogle Scholar
  85. 85.
    Hue MX, Zhang XM, Gong LZ (2008) Synlett 691Google Scholar
  86. 86.
    Chen XH, Zhang WQ, Gong LZ (2008) J Am Chem Soc 130:5652CrossRefGoogle Scholar
  87. 87.
    Guo C, Xue MX, Zhu MK, Gong LZ (2008) Angew Chem Int Edit 47:3414CrossRefGoogle Scholar
  88. 88.
    Che W, Du W, Duan YZ, Wu Y, Yang SY, Chen YC (2007) Angew Chem Int Edit 46:7667CrossRefGoogle Scholar
  89. 89.
    Chen W, Yuan XH, Li R, Du W, Wu Y, Ding LS, Chen YC (2006) Adv Synth Catal 348:1818CrossRefGoogle Scholar
  90. 90.
    Pinto N, Fleury-Brégeot N, Marinetti A (2009) Eur J Org Chem 146CrossRefGoogle Scholar
  91. 91.
    For the discussion of organocatalysis on water, see: (a) Brogan AP, Dickerson TJ, Janda KD (2006) Angew Chem Int Edit 45:8100; (b) Hayashi Y (2006) Angew Chem Int Edit 45:8103; (c) Blackmond DG, Armstrong A, Coombe V, Wells A (2007) Angew Chem Int Edit 46:3798Google Scholar
  92. 92.
    (a) González-Cruz D, Tejedor D, de Armas P, García-Tellado F (2007) Chem Eur J 13:4823; (b) González-Cruz D, Tejedor D, de Armas P, Morales ED, García-Tellado F (2006) Chem Comm 2798Google Scholar
  93. 93.
    Hong BC, Liu KL, Tsai CW, Liao JH (2008) Tetrahedron Lett 49:5480CrossRefGoogle Scholar
  94. 94.
    Ramachary DB, Ramakumar K, Narayana VV (2008) Chem Eur J 14:9143CrossRefGoogle Scholar
  95. 95.
    For reviews on phosphine catalyzed reactions, see: (a) Lu X, Zhang C, Xu Z (2001) Acc Chem Res 34:535; (b) Methot JL, Roush WR (2004) Adv Synth Catal 346:1035; (c) Ye LW, Zhou J, Tang Y (2008) Chem Soc Rev 37:1140Google Scholar
  96. 96.
    For examples, see: (a) Jean L, Marinetti A (2006) Tetrahedron Lett 47:2141 (b) Zhu XF, Henry CE, Kwon O (2005) Tetrahedron 61:6276 (c) Fleury-Brégeot N, Jean L, Retailleau P, Marinetti A (2007) Tetrahedron 63:11920 (d) Panossian A, Fleury-Brégeot N, Marinetti A (2008) Eur J Org Chem 3826 (e) Liang Y, Liu S, Xia Y, Li Y, Yu ZX (2008) Chem Eur J 14:4361 (f) Xia Y, Liang Y, Chen Y, Wang M, Jiao L, Huang F, Liu S, Li Y, Yu ZX (2007) J Am Chem Soc 129:3470 (g) Liang Y, Liu S, Yu ZX (2009) Synlett 905 (h) Kumar K, Kapoor R, Kapur A, Ishar MPS (2000) Org Lett 2:2023Google Scholar
  97. 97.
    Hones RA, Krische MJ (2009) Org Lett 2009(11):1849Google Scholar
  98. 98.
    Xu S, Zhou L, Ma R, Song H, He Z (2009) Chem Eur J 15:8698CrossRefGoogle Scholar
  99. 99.
    Schuler M, Duvvuru D, Retailleau P, Betzer JF, Marinetti A (2009) Org Lett 11:4406CrossRefGoogle Scholar
  100. 100.
    Müller S, List B (2009) Angew Chem Int Edit 48:9975CrossRefGoogle Scholar
  101. 101.
    Maciver EE, Thompson S, Smith MD (2009) Angew Chem Int Edit 48:9979CrossRefGoogle Scholar
  102. 102.
    For recent reviews in multicomponent reactions, see: (a) Zhu J, Bienaymé H (2005) Multicomponent reactions. Wiley-VCH, Weinheim; (b) Guillena G, Ramón DJ, Yus M (2007) Tetrahedron: Asymmetr 18:693Google Scholar
  103. 103.
    Chen XH, Wei Q, Luo SW, Xiao H, Gong LZ (2009) J Am Chem Soc 131:13819CrossRefGoogle Scholar
  104. 104.
    Jiang J, Qing J, Gong LZ (2009) Chem Eur J 15:7031CrossRefGoogle Scholar
  105. 105.
    Zou Y, Wang Q, Goeke A (2008) Chem Eur J 14:5335CrossRefGoogle Scholar
  106. 106.
    Rios R, Ibrahem I, Vesely J, Zhao GL, Cordova A (2007) Tetrahedron Lett 48:5701CrossRefGoogle Scholar
  107. 107.
    Zhu D, Lu M, Dai L, Zhong G (2009) Angew Chem Int Edit 48:6089CrossRefGoogle Scholar
  108. 108.
    The same reaction reported earlier by Hong’s group, see: Hong BC, Nimje RY, Wu MF, Sadani AA (2008) Eur J Org Chem 1449Google Scholar
  109. 109.
    Vesely J, Rios R, Ibrahem I, Zhao GL, Eriksson L, Córdova A (2008) Chem Eur J 14:2693CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  1. 1.Department of Chemistry and BiochemistryNational Chung Cheng UniversityChiayi 621Taiwan, R.O.C

Personalised recommendations