Water as Reaction Medium in the Synthetic Processes Involving Epoxides

  • Daniela Lanari
  • Oriana Piermatti
  • Ferdinando Pizzo
  • Luigi Vaccaro


There is much chemistry between water and epoxide. This contribution deals with the use of water in processes based on the epoxide ring opening. Reported examples highlight the role of water not as a simple substitution of the organic medium or as an exotic option to claim the greenness of a process, but also show the role of this medium for reaching the highest chemical efficiency. The peculiar properties of water have allowed to realize processes that sometimes cannot even be performed in other reaction media.


Ring Opening Styrene Oxide Cyclohexene Oxide Dioctyl Sulfosuccinate Vinyl Sulfide 
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.



We gratefully acknowledge the Ministero dell’Istruzione, dell’Università e della Ricerca (MIUR) and the Università degli Studi di Perugia within the projects “Firb–Futuro in Ricerca” (prot. n. RBFR08TTWW and prot. n. RBFR08J78Q), PRIN 2008 for financial support.


  1. 1.
    Gruttadauria M, Giacalone F, Noto R (2009) Water in stereoselective organocatalytic reactions. Adv Synth Catal 351:33–57CrossRefGoogle Scholar
  2. 2.
    Kobayashi S (2007) Asymmetric catalysis in aqueous media. Pure Appl Chem 79:235–245CrossRefGoogle Scholar
  3. 3.
    Lindström UM (2007) Organic synthesis in water. Blackwell, LondonGoogle Scholar
  4. 4.
    Hayashi Y (2006) In water or in the presence of water? Angew Chem Int Ed 45:8103–8104CrossRefGoogle Scholar
  5. 5.
    Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB (2005) “On water”: unique reactivity of organic compounds in aqueous suspension. Angew Chem Int Ed 44:3275–3279CrossRefGoogle Scholar
  6. 6.
    Li C-J (2005) Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem Rev 105:3095–3165CrossRefGoogle Scholar
  7. 7.
    Fringuelli F, Piermatti O, Pizzo F, Vaccaro L (2001) Recent advances in Lewis acid catalyzed Diels-Alder reactions in aqueous media. Eur J Org Chem 2001:439–455CrossRefGoogle Scholar
  8. 8.
    Reichardt C (ed) (1990) Solvents and solvent effects in organic chemistry. VCH, WeinhemGoogle Scholar
  9. 9.
    Vilotijevic I, Jamison TF (2009) Epoxide-opening cascades in the synthesis of polycyclic polyether natural products. Angew Chem Int Ed 48:5250–5281CrossRefGoogle Scholar
  10. 10.
    Bergmeier SC, Lapinsky DJ (2009) Three-membered ring systems. Prog Heterocycl Chem 21:69–93CrossRefGoogle Scholar
  11. 11.
    Pineschi M, Bertolini F, Di Bussolo V, Crotti P (2009) Regio- and stereoselective ring opening of allylic epoxides. Curr Org Synth 6:290–324CrossRefGoogle Scholar
  12. 12.
    Morten CJ, Byers AJ, Van Dyke AR, Vilotijevic I, Jamison TF (2009) The development of endo-selective epoxide-opening cascades in water. Chem Soc Rev 38:3175–3192CrossRefGoogle Scholar
  13. 13.
    Schneider C (2006) Synthesis of 1,2-difunctionalized fine chemicals through catalytic, enantioselective ring-opening reactions of epoxides. Synthesis 2919–2944Google Scholar
  14. 14.
    Pastor IM, Yus M (2005) Asymmetric ring opening of epoxides. Curr Org Chem 9:1–29CrossRefGoogle Scholar
  15. 15.
    Smith JG (1984) Synthetically useful reactions of epoxides. Synthesis 629–656Google Scholar
  16. 16.
    Parker RE, Isaacs NS (1959) Mechanisms of epoxide reactions. Chem Rev 59(4):737–799CrossRefGoogle Scholar
  17. 17.
    Wong OA, Shi Y (2008) Organocatalytic oxidation asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts. Chem Rev 108:3958–3987CrossRefGoogle Scholar
  18. 18.
    Jacobsen EN (2000) Asymmetric catalysis of epoxide ring-opening reactions. Acc Chem Res 33:421–433CrossRefGoogle Scholar
  19. 19.
    Bedore MW, Zaborenko N, Jensen KF, Jamison TF (2010) Aminolysis of epoxides in a microreactor system: a continuous flow approach to β-amino alcohols. Org Process Res Dev 14:432–440CrossRefGoogle Scholar
  20. 20.
    Heravi MM, Baghernejad B, Oskooie HA (2009) A new strategy for the aminolysis of epoxides with amines under solvent-free conditions using Fe-Mcm-41 as a novel and efficient catalyst. Catal Lett 130:547–550CrossRefGoogle Scholar
  21. 21.
    Ollevier T, Nadeau E (2008) Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines. Tetrahedron Lett 49:1546–1550CrossRefGoogle Scholar
  22. 22.
    Shivani PB, Chakraborti AK (2007) Zinc(II) perchlorate hexahydrate catalyzed opening of epoxide ring by amines: applications to synthesis of (RS)/(R)-propranolols and (RS)/(R)/(S)-naftopidils. J Org Chem 72:3713–3722CrossRefGoogle Scholar
  23. 23.
    Yarapathy VR, Mekala S, Rao BV, Tammishetti S (2006) Polymer supported copper sulphate promoted aminolysis of epoxides with aromatic amines. Catal Commun 7:466–471CrossRefGoogle Scholar
  24. 24.
    Sarangi C, Das N B, Nanda B, Nayak A, Sharma RP (1997) An Efficient nucleophilic cleavage of oxiranes to 1,2-azido alcohols. J Chem Res (S) 378–379Google Scholar
  25. 25.
    Crotti P, Di Bussolo V, Favero L, Macchia F, Pineschi M (1996) A novel effective transition metal based salt-catalyzed azidolysis of 1,2-epoxides. Tetrahedron Lett 37:1675–1678CrossRefGoogle Scholar
  26. 26.
    Meguro M, Asao N, Yamamoto Y (1995) Ytterbium triisopropoxide catalysed ring opening of epoxides with trimethylsilyl azide. J Chem Soc Chem Commun 1021–1022Google Scholar
  27. 27.
    Mereyala HB, Frei B (1986) Preparation of vicinal azidohydrins by reaction of oxiranes with triethylaluminium/hydrogen azide. Helv Chim Acta 69:415–418CrossRefGoogle Scholar
  28. 28.
    Burfield DR, Gan S, Smithers RH (1977) Reactions of a mono- and a tri-substituted epoxide with some simple and β-substituted primary amines; novel examples of electrophilic anchimeric assistance. J Chem Soc Perkin Trans I 666–671Google Scholar
  29. 29.
    Sundaram PK, Sharma MM (1969) Kinetics of reactions of amines with alkene oxides. Bull Chem Soc Jpn 42:3141–3147CrossRefGoogle Scholar
  30. 30.
    FAN R-H, Hou X-L (2003) Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water. J Org Chem 68:726–730CrossRefGoogle Scholar
  31. 31.
    Wu J, Xia H-G (2005) Tertiary amines as highly efficient catalysts in the ring–opening reactions of epoxides with amines or thiols in H2O: expeditious approach to β-amino alcohols and β-aminothioethers. Green Chem 7:708–710CrossRefGoogle Scholar
  32. 32.
    Azizi N, Saidi MR (2005) Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1. Org Lett 7:3649–3651CrossRefGoogle Scholar
  33. 33.
    Surendra K, Krishnaveni NS, Rao KR (2005) The selective C-3 opening of aromatic 2,3-epoxy alcohols/epoxides with aromatic amines catalysed by β-cyclodextrin in water. Synlett 506–510Google Scholar
  34. 34.
    Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2005) InCl3-catalyzed regio- and stereoselective thiolysis of α-epoxycarboxylic acids in water. Org Lett 7:4411–4414CrossRefGoogle Scholar
  35. 35.
    Fringuelli F, Pizzo F, Vaccaro L (2004) NaOH-catalyzed thiolysis of a, b-epoxyketones in water. A key step in the synthesis of target molecules starting from α,-unsaturated ketones. J Org Chem 69:2315–2321CrossRefGoogle Scholar
  36. 36.
    Fioroni G, Fringuelli F, Pizzo F, Vaccaro L (2003) Epoxidation of α, βunsaturated ketones in water. An environmentally benign protocol. Green Chem 5:425–428CrossRefGoogle Scholar
  37. 37.
    Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2003) Zn(II)-catalyzed thiolysis of oxiranes in water under neutral conditions. J Org Chem 68:8248–8251CrossRefGoogle Scholar
  38. 38.
    Fringuelli F, Pizzo F, Rucci M, Vaccaro L (2003) First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water. A new protocol for preparation of optically active norstatines. J Org Chem 68:7041–7045CrossRefGoogle Scholar
  39. 39.
    Amantini D, Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2003) ZnCl2. as an efficient catalyst in the thiolysis of 1,2-epoxides by thiophenol in aqueous medium. Synlett 2292–2296Google Scholar
  40. 40.
    Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2003) Easy and environmentally friendly uncatalyzed synthesis of β-hydroxy arylsulfides by thiolysis of 1,2-epoxides in water. Green Chem 5:436–440CrossRefGoogle Scholar
  41. 41.
    Amantini D, Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2002) Nucleophilic ring opening of 1,2-epoxides in aqueous medium. Arkivoc (xi):293–311Google Scholar
  42. 42.
    Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2002) Thiolysis of alkyl- and aryl-1,2-epoxides in water catalyzed by InCl3. Adv Synth Catal 344:379–384CrossRefGoogle Scholar
  43. 43.
    Fringuelli F, Pizzo F, Vaccaro L (2001) Azidolysis of α, β-epoxycarboxylic acids. A water-promoted process efficiently catalyzed by indium trichloride at pH 4.0. J Org Chem 66:3554–3558CrossRefGoogle Scholar
  44. 44.
    Fringuelli F, Pizzo F, Vaccaro L (2001) Lewis acid catalyzed organic reactions in water. The case of AlCl3, TiCl4, and SnCl4 believed to be unusable in aqueous medium. J Org Chem 66:4719–4722CrossRefGoogle Scholar
  45. 45.
    Amantini D, Fringuelli F, Pizzo F, Vaccaro L (2001) Bromolysis and iodolysis of α, β-epoxycarboxylic acids in water catalyzed by indium halides. J Org Chem 66:4463–4467CrossRefGoogle Scholar
  46. 46.
    Fringuelli F, Pizzo F, Vaccaro L (2001) AlCl3 as an efficient Lewis acid catalyst in water. Tetrahedron Lett 42:1131–1133CrossRefGoogle Scholar
  47. 47.
    Fringuelli F, Pizzo F, Vaccaro L (2000) First efficient regio- and stereoselective metal-­catalyzed azidolysis of 2,3-epoxycarboxylic acids in water. Synlett 311–314Google Scholar
  48. 48.
    Fringuelli F, Piermatti O, Pizzo F, Vaccaro L (1999) Ring opening of epoxides with sodium azide in water. A regioselective pH-controlled reaction. J Org Chem 64:6094–6096CrossRefGoogle Scholar
  49. 49.
    Bonollo S, Fringuelli F, Pizzo F, Vaccaro L (2006) A green route to β-amino alcohols via the uncatalyzed aminolysis of 1,2-epoxides by alkyl- and arylamines. Green Chem 8:960–964CrossRefGoogle Scholar
  50. 50.
    Abaee MS, Hamidi V, Mojtahedi MM (2008) Ultrasound promoted aminolysis of epoxides in aqueous media: a rapid procedure with no pH adjustment for additive-free synthesis of β-aminoalcohols. Ultrason Sonochem 15:823–827CrossRefGoogle Scholar
  51. 51.
    Sreedhar B, Radhika P, Neelima B, Hebalkar N (2007) Regioselective ring opening of epoxides with amines using monodispersed silica nanoparticles in water. J Mol Catal A 272:159–163CrossRefGoogle Scholar
  52. 52.
    Procopio A, Gaspari M, Nardi M, Oliverio M, Rosati O (2008) Highly efficient and versatile chemoselective addition of amines to epoxides in water catalyzed by erbium(III) triflate. Tetrahedron Lett 49:2289–2293CrossRefGoogle Scholar
  53. 53.
    Bonollo S, Fringuelli F, Pizzo F, Vaccaro L. (2007) Zr(DS)4 as an efficient catalyst for the aminolysis of epoxides in water. Synlett 2683–2686Google Scholar
  54. 54.
    Firouzabadi H, Iranpoor N, Khoshnood A (2007) Aluminum tris (dodecyl sulfate) trihydrate Al(DS)3·3H2O as an efficient Lewis acid–surfactant-combined catalyst for organic reactions in water: efficient conversion of epoxides to thiiranes and to amino alcohols at room temperature. J Mol Catal A 274:109–115CrossRefGoogle Scholar
  55. 55.
    Kobayashi S, Manabe K (2002) Development of novel Lewis acid catalysts for selective organic reactions in aqueous media. Acc Chem Res 35:209–217CrossRefGoogle Scholar
  56. 56.
    Azoulay S, Manabe K, Kobayashi S (2005) Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water. Org Lett 7:4593–4595CrossRefGoogle Scholar
  57. 57.
    Ogawa C, Azoulay S, Kobayashi S (2005) Bismuth triflate-chiral bipyridine complex catalyzed asymmetric ring opening reactions of meso-epoxide in water. Heterocycles 66:201–206CrossRefGoogle Scholar
  58. 58.
    Schneider C, Sreekanth AR, Mai E (2004) Scandium-bipyridine-catalyzed enantioselective addition of alcohols and amines to meso-epoxides. Angew Chem Int Ed 43:5691–5694CrossRefGoogle Scholar
  59. 59.
    Tschöp A, Marx A, Sreekanth AR, Schneider C (2007) Scandium-bipyridine-catalyzed enantioselective alcoholysis of meso-epoxides. Eur J Org Chem 2007:2318–2327CrossRefGoogle Scholar
  60. 60.
    Bonollo S, Fringuelli F, Pizzo F, Vaccaro L (2008) Zn(II)-catalyzed desymmetrization of meso-epoxides by aromatic amines in water. Synlett 1574–1578Google Scholar
  61. 61.
    Kokubo M, Naito T, Kobayashi S (2010) Chiral zinc(II) and copper(II)-catalyzed asymmetric ring-opening reactions of meso-epoxides with aniline and indole derivatives. Tetrahedron 66:1111–1118CrossRefGoogle Scholar
  62. 62.
    Boudou M, Ogawa C, Kobayashi S (2006) Chiral scandium-catalysed enantioselective ring-opening of meso-epoxides with N-heterocycle alcohol and thiol derivatives in water. Adv Synth Catal 348:2585–2589CrossRefGoogle Scholar
  63. 63.
    Iranpoor N, Firouzabadi H, Shekarize M (2003) Micellar media for the efficient ring opening of epoxides with CN, N3, NO3, NO2, SCN, Cl and Br catalyzed with Ce(OTf)4. Org Biomol Chem 1:724–727CrossRefGoogle Scholar
  64. 64.
    (a) Patai S (1971) The Chemistry of the azido group. Wiley, New York; (b) Scriven EFV, Turnbull K (1988) Chem Rev 88:297–368Google Scholar
  65. 65.
    Kiasat A-R, Zayadi M (2008) Polyethylene glycol immobilized on silica gel as a new solid–liquid phase-transfer catalyst for regioselective azidolysis of epoxides in water: an efficient route to 1,2-azido alcohols. Catal Commun 9:2063–2067CrossRefGoogle Scholar
  66. 66.
    Kiasat A-R, Badri R, Zargar B, Sayyahi S (2008) Poly(ethylene glycol) grafted onto dowex resin: an efficient, recyclable, and mild polymer-supported phase transfer catalyst for the regioselective azidolysis of epoxides in water. J Org Chem 73:8382–8385CrossRefGoogle Scholar
  67. 67.
    Various Authors (1999) The chemistry and biology of β-amino acids. In: Hoekstra WJ (ed) Curr Med Chem 6:905–1002Google Scholar
  68. 68.
    Kiso Y, Yamaguchi S, Matsumoto H et al (1998) KNI-577, a potent small-sized HIV protease inhibitor based on the dipeptide containing the hydroxymethylcarbonyl isostere as an ideal transition-state mimic. Arch Pharm 331:87–89CrossRefGoogle Scholar
  69. 69.
    Juaristi E (1997) Enantioselective synthesis of β-amino acids. Wiley-VCH, New YorkGoogle Scholar
  70. 70.
    Cardillo G, Tomasini C (1996) Asymmetric synthesis of ß-amino acids and α-substituted β-amino acids. Chem Soc Rev 25:117–127CrossRefGoogle Scholar
  71. 71.
    Azzena F, Crotti P, Favero L, Pineschi M (1995) Regiochemical control of the ring opening of 12-epoxides by means of chelating processes.11. Ring opening reactions of aliphatic mono- and difunctionalized cis and trans 2,3- and 3,4-epoxy esters. Tetrahedron 48:13409–13422CrossRefGoogle Scholar
  72. 72.
    Legters J, Thijs L, Zwanenburg B (1992) A convenient synthesis of aziridine-2-carboxylic esters. Recl Trav Chim Pays-Bas 111:1–23CrossRefGoogle Scholar
  73. 73.
    Chong JM, Sharpless KB (1985) Nucleophilic openings of 2,3-epoxy acids and amides mediated by Ti(O-i-Pr)4. Reliable C-3 selectivity. J Org Chem 50:1560–1563CrossRefGoogle Scholar
  74. 74.
    Fringuelli F, Pizzo F, Vaccaro L (2000) Cobalt(II) chloride-catalyzed chemoselective sodium borohydride reduction of azides in water. Synthesis 646–650Google Scholar
  75. 75.
    Jafarpour M, Rezaeifard A, Aliabadi M (2010) An environmentally benign catalytic method for efficient and selective nucleophilic ring opening of oxiranes by zirconium tetrakis(dodecyl sulfate). Helv Chim Acta 93:405–413CrossRefGoogle Scholar
  76. 76.
    Kamal A, Arifuddin M, Rao MV (1999) Enantioselective ring opening of epoxides with trimethylsilyl azide (TMSN3) in the presence of β-cyclodextrin: an efficient route to 1,2-azido alcohols. Tetrahedron Asymmetry 10:4261–4264CrossRefGoogle Scholar
  77. 77.
    Guy A, Doussout J, Garreau R, Godefroy-Falguieres A (1992) Selective ring-opening reaction of styrene oxide with lithium azide in the presence of cyclodextrins in aqueous media. Tetrahedron Asymmetry 2:247–250CrossRefGoogle Scholar
  78. 78.
    As recent efficient example and literature update see Zvagulis A, Bonollo S, Lanari D, Pizzo F, Vaccaro L (2010). 2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene (PS-BEMP) as an efficient recoverable and reusable catalyst for the phenolysis of epoxides under solvent-free conditions. Adv Synth Catal 352:2489–2496Google Scholar
  79. 79.
    Jiang D, Urakawa A, Yulikov M, Mallat M, Jeschke T, Baiker A (2009) Size selectivity of a copper metal-organic framework and origin of catalytic activity in epoxide alcoholysis. Chem Eur J 15:12255–12262CrossRefGoogle Scholar
  80. 80.
    Brimble MA, Liu Y-C, Trzoss M (2007) A facile synthesis of aryl spirodioxines based on a 3 h,3′h-2,2′-spiro­bi(benzo[b][1,4]dioxine) skeleton. Synthesis 1392–1402Google Scholar
  81. 81.
    Rossbach BM, Leopold K, Weberskirch R (2006) Self-assembled nanoreactors as highly active catalysts in the hydrolytic kinetic resolution (HKR) of epoxides in water. Angew Chem Int Ed 45:1309–1312CrossRefGoogle Scholar
  82. 82.
    Song Y, Yao X, Chen H, Bai C, Hu X, Zheng Z (2002) Highly enantioselective resolution of terminal epoxides using polymeric catalysts. Tetrahedron Lett 42:6625–6627CrossRefGoogle Scholar
  83. 83.
    Boersma AJ, Feringa BL, Roelfes G (2007) α, β-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-based catalytic asymmetric Diels-Alder reaction in water. Org Lett 9:3647–3650CrossRefGoogle Scholar
  84. 84.
    Roelfes G, Boersma A J, Feringa B L (2006) Highly enantioselective DNA-based catalysis. Chem Commun 635–637Google Scholar
  85. 85.
    Roelfes G, Feringa BL (2005) DNA-based asymmetric catalysis. Angew Chem Int Ed 44:3230–3232CrossRefGoogle Scholar
  86. 86.
    Dijk EW, Feringa BL, Roelfes G (2008) DNA-based hydrolytic kinetic resolution of epoxides. Tetrahedron Asymmetry 19:2374–2377CrossRefGoogle Scholar
  87. 87.
    van der Werf MJ, Jongejan H, Franssen MCR (2001) Resolution of limonene 1,2-epoxide diastereomers by mercury(II) ions. Tetrahedron Lett 42:5521–5524CrossRefGoogle Scholar
  88. 88.
    Reddy MA, Bhanumathi N, Rao KR (2002) (2002) A mild and efficient biomimetic synthesis of α-hydroxymethylarylketones from oxiranes in the presence of β-cyclodextrin and NBS in water. Tetrahedron Lett 43:3237–3238CrossRefGoogle Scholar
  89. 89.
    Surendra K, Krishnaveni NS, Reddy MA, Nageswar YVD, Rao KR (2003) Highly selective oxidative cleavage of β-cyclodextrin-epoxide/aziridine complexes with ibx in water. J Org Chem 68:9119–9121CrossRefGoogle Scholar
  90. 90.
    Furutani T, Imashiro R, Hatsuda M (2002) A practical procedure for the large-scale preparation of methyl (2R,3 S)-3-(4-methoxyphenyl)glycidate, a key intermediate for diltiazem. J Org Chem 67:4599–4601CrossRefGoogle Scholar
  91. 91.
    Adams H, Bell R, Cheung Y-Y, Jones ND, Tomkinson NCO (1999) The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)- and (−)-trans-1-mercaptocyclohexan-2-ol. Tetrahedron Asymmetry 10:4129–4142CrossRefGoogle Scholar
  92. 92.
    Justo De Pomar JC, Soderquist A (1998) Regio- and stereospecific synthesis of (O-TIPS)-protected 2-hydroxyalkylmercaptans from epoxides and triisopropylsilanethiol. Tetrahedron Lett 39:4409–4412CrossRefGoogle Scholar
  93. 93.
    Yamada O, Ogasawara K, Synlett 427–428Google Scholar
  94. 94.
    Behrens CH, Sharpless KB (1985) Selective transformations of 2,3-epoxy alcohols and related derivatives. Strategies for nucleophilic attack at carbon-3 or carbon-2. J Org Chem 50:5696–5704CrossRefGoogle Scholar
  95. 95.
    Abul-Hajj YJ (1986) Synthesis and evaluation of 4-(substituted thio)-4-androstene-3,17-dione derivatives as potential aromatase inhibitors. J Med Chem 29:582–584CrossRefGoogle Scholar
  96. 96.
    Smith MB, March MB (2001) March’s advanced organic chemistry, 5th edn. Wiley-Interscience Publication, New YorkGoogle Scholar
  97. 97.
    Streitwieser A (1952) Solvolytic displacement reactions at saturated carbon atoms. Chem Rev 56:571, cfr. page 582CrossRefGoogle Scholar
  98. 98.
    Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2005) Thiolysis of 1,2-epoxides under environmentally friendly conditions. Targets Heterocycl Syst 8:147–161Google Scholar
  99. 99.
    Lauret C (2001) Epoxy ketones as versatile building blocks in organic synthesis. Tetrahedron Asymmetry Rep N 52(12):2359–2383CrossRefGoogle Scholar
  100. 100.
    Fringuelli F, Pizzo F, Tortoioli S, Zuccaccia C, Vaccaro L (2006) In(OTf)3-catalyzed thiolysis of 1,2-epoxides by arylthiols under SFC. A new approach for the synthesis of thiazolopyridinium ionic liquids. Green Chem 8:191–196CrossRefGoogle Scholar
  101. 101.
    Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2004) Solvent-free Al(OTf)3-catalyzed aminolysis of 1,2-epoxides by 2-picolylamine: a key step in the synthesis of ionic liquids. J Org Chem 69:7745–7747CrossRefGoogle Scholar
  102. 102.
    Murthy SN, Madhav B, Reddy VP, Rao KR, Nageswar YVD (2009) An approach toward the synthesis of β-hydroxy sulfones on water. Tetrahedron Lett 50:5009–5011CrossRefGoogle Scholar
  103. 103.
    Pironti V, Colonna S (2005) In(OTf)3-catalyzed thiolysis of 1,2-epoxides by arylthiols under SFC. A new approach for the synthesis of thiazolopyridinium ionic liquids. Green Chem 7:43–45CrossRefGoogle Scholar
  104. 104.
    Kiasat AR, Mirzajani R, Shalbaf H, Tabatabaei T (2009) Nucleophilic ring opening of epoxides promoted by multi-site phase-transfer catalyst. An efficient and eco-friendly route to synthesis of β-hydroxy-thiocyanate. Chin Chem Lett 20:1025–1029CrossRefGoogle Scholar
  105. 105.
    Kiasat AR, Mehrjardi MF (2008) PEG-SO3H as eco-friendly polymeric catalyst for regioselective ring opening of epoxides using thiocyanate anion in water: an efficient route to ­synthesis of β-hydroxy thiocyanate. Catal Commun 9:1497–1500CrossRefGoogle Scholar
  106. 106.
    Gao P, Xu P-F, Zhai H (2008) Borax-catalyzed thiolysis of 1,2-epoxides in aqueous medium. Tetrahedron Lett 49:6536–6538CrossRefGoogle Scholar
  107. 107.
    Kokubo M, Naito T, Kobayashi S (2009) Metal-controlled reversal of enantioselectivity in catalyzed asymmetric ring-opening reactions of meso-epoxides in water. Chem Lett 38:904–905CrossRefGoogle Scholar
  108. 108.
    Srinivas B, Kumar VP, Sridhar R, Surendra K, Nageswar YVD, Rao KR (2007) Regioselective nucleophilic opening of epoxides and aziridines under neutral conditions in the presence of β-cyclodextrin in water. J Mol Catal A 261:1–5CrossRefGoogle Scholar
  109. 109.
    Sridhar R, Srinivas B, Surendra K, Krishnaveni NS, Rao KR (2005) Synthesis of β-hydroxy selenides using benzeneselenol and oxiranes under supramolecular catalysis in the presence of β-cyclodextrin in water. Tetrahedron Lett 46:8837–8839CrossRefGoogle Scholar
  110. 110.
    Concellón JM, Bardales E, Gómez C (2003) 1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues. Tetrahedron Lett 44:5323–5326CrossRefGoogle Scholar
  111. 111.
    Doussot J, Guy A, Siaugue J-M, Ferroud C, Falguieres A (1999) Substituent effects in the selective reductive opening of epoxides with borohydrides in the presence of β-cyclodextrin. Chirality 11:541–545CrossRefGoogle Scholar
  112. 112.
    Doussot J, Guy A, Garreau R, Falguières A, Cossy J, Amsterdamsky C (1996) Préparation sélective d’alcools benzyliques substitutés à partir de substrats aromatiques complexés dans la b–cyclodextrine. Bull Soc Chim Fr 133:161–166CrossRefGoogle Scholar
  113. 113.
    Hu Y, Uno M, Harada A, Takahashi S (1991) Selective ring–opening reaction of epoxides with sodium borohydride in the presence of cyclodextrins in aqueous media. Bull Chem Soc Jpn 64:1884–1888CrossRefGoogle Scholar
  114. 114.
    Hu Y, Uno M, Harada A, Takahashi S (1990) Selective ring–opening reaction of epoxides with sodium borohydride in the presence of cyclodextrins in aqueous media. Chem Lett 797–798CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Daniela Lanari
    • 1
  • Oriana Piermatti
    • 1
  • Ferdinando Pizzo
    • 1
  • Luigi Vaccaro
    • 1
  1. 1.Laboratory of Green Synthetic Organic Chemistry, CEMIN–Dipartimento di ChimicaUniversità di PerugiaPerugiaItaly

Personalised recommendations