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Water as Reaction Medium in the Synthetic Processes Involving Epoxides

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Abstract

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.

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References

  1. Gruttadauria M, Giacalone F, Noto R (2009) Water in stereoselective organocatalytic reactions. Adv Synth Catal 351:33–57

    Article  CAS  Google Scholar 

  2. Kobayashi S (2007) Asymmetric catalysis in aqueous media. Pure Appl Chem 79:235–245

    Article  CAS  Google Scholar 

  3. Lindström UM (2007) Organic synthesis in water. Blackwell, London

    Google Scholar 

  4. Hayashi Y (2006) In water or in the presence of water? Angew Chem Int Ed 45:8103–8104

    Article  CAS  Google Scholar 

  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 44:3275–3279

    Article  CAS  Google Scholar 

  6. Li C-J (2005) Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem Rev 105:3095–3165

    Article  CAS  Google Scholar 

  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 2001:439–455

    Article  Google Scholar 

  8. Reichardt C (ed) (1990) Solvents and solvent effects in organic chemistry. VCH, Weinhem

    Google Scholar 

  9. Vilotijevic I, Jamison TF (2009) Epoxide-opening cascades in the synthesis of polycyclic polyether natural products. Angew Chem Int Ed 48:5250–5281

    Article  CAS  Google Scholar 

  10. Bergmeier SC, Lapinsky DJ (2009) Three-membered ring systems. Prog Heterocycl Chem 21:69–93

    Article  CAS  Google Scholar 

  11. Pineschi M, Bertolini F, Di Bussolo V, Crotti P (2009) Regio- and stereoselective ring opening of allylic epoxides. Curr Org Synth 6:290–324

    Article  CAS  Google Scholar 

  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 38:3175–3192

    Article  CAS  Google Scholar 

  13. Schneider C (2006) Synthesis of 1,2-difunctionalized fine chemicals through catalytic, enantioselective ring-opening reactions of epoxides. Synthesis 2919–2944

    Google Scholar 

  14. Pastor IM, Yus M (2005) Asymmetric ring opening of epoxides. Curr Org Chem 9:1–29

    Article  CAS  Google Scholar 

  15. Smith JG (1984) Synthetically useful reactions of epoxides. Synthesis 629–656

    Google Scholar 

  16. Parker RE, Isaacs NS (1959) Mechanisms of epoxide reactions. Chem Rev 59(4):737–799

    Article  CAS  Google Scholar 

  17. Wong OA, Shi Y (2008) Organocatalytic oxidation asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts. Chem Rev 108:3958–3987

    Article  CAS  Google Scholar 

  18. Jacobsen EN (2000) Asymmetric catalysis of epoxide ring-opening reactions. Acc Chem Res 33:421–433

    Article  CAS  Google Scholar 

  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 14:432–440

    Article  CAS  Google Scholar 

  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 130:547–550

    Article  CAS  Google Scholar 

  21. Ollevier T, Nadeau E (2008) Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines. Tetrahedron Lett 49:1546–1550

    Article  CAS  Google Scholar 

  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 72:3713–3722

    Article  CAS  Google Scholar 

  23. Yarapathy VR, Mekala S, Rao BV, Tammishetti S (2006) Polymer supported copper sulphate promoted aminolysis of epoxides with aromatic amines. Catal Commun 7:466–471

    Article  CAS  Google Scholar 

  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) 378–379

    Google Scholar 

  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 37:1675–1678

    Article  CAS  Google Scholar 

  26. Meguro M, Asao N, Yamamoto Y (1995) Ytterbium triisopropoxide catalysed ring opening of epoxides with trimethylsilyl azide. J Chem Soc Chem Commun 1021–1022

    Google Scholar 

  27. Mereyala HB, Frei B (1986) Preparation of vicinal azidohydrins by reaction of oxiranes with triethylaluminium/hydrogen azide. Helv Chim Acta 69:415–418

    Article  CAS  Google Scholar 

  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 666–671

    Google Scholar 

  29. Sundaram PK, Sharma MM (1969) Kinetics of reactions of amines with alkene oxides. Bull Chem Soc Jpn 42:3141–3147

    Article  CAS  Google Scholar 

  30. FAN R-H, Hou X-L (2003) Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water. J Org Chem 68:726–730

    Article  CAS  Google Scholar 

  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 7:708–710

    Article  CAS  Google Scholar 

  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 7:3649–3651

    Article  CAS  Google Scholar 

  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 506–510

    Google Scholar 

  34. Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2005) InCl3-catalyzed regio- and stereoselective thiolysis of α-epoxycarboxylic acids in water. Org Lett 7:4411–4414

    Article  CAS  Google Scholar 

  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 69:2315–2321

    Article  CAS  Google Scholar 

  36. Fioroni G, Fringuelli F, Pizzo F, Vaccaro L (2003) Epoxidation of α, βunsaturated ketones in water. An environmentally benign protocol. Green Chem 5:425–428

    Article  CAS  Google Scholar 

  37. Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2003) Zn(II)-catalyzed thiolysis of oxiranes in water under neutral conditions. J Org Chem 68:8248–8251

    Article  CAS  Google Scholar 

  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 68:7041–7045

    Article  CAS  Google Scholar 

  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 2292–2296

    Google Scholar 

  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 5:436–440

    Article  CAS  Google Scholar 

  41. Amantini D, Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2002) Nucleophilic ring opening of 1,2-epoxides in aqueous medium. Arkivoc (xi):293–311

    Google Scholar 

  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 344:379–384

    Article  CAS  Google Scholar 

  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 66:3554–3558

    Article  CAS  Google Scholar 

  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 66:4719–4722

    Article  CAS  Google Scholar 

  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 66:4463–4467

    Article  CAS  Google Scholar 

  46. Fringuelli F, Pizzo F, Vaccaro L (2001) AlCl3 as an efficient Lewis acid catalyst in water. Tetrahedron Lett 42:1131–1133

    Article  CAS  Google Scholar 

  47. Fringuelli F, Pizzo F, Vaccaro L (2000) First efficient regio- and stereoselective metal-­catalyzed azidolysis of 2,3-epoxycarboxylic acids in water. Synlett 311–314

    Google Scholar 

  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 64:6094–6096

    Article  CAS  Google Scholar 

  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 8:960–964

    Article  CAS  Google Scholar 

  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 15:823–827

    Article  CAS  Google Scholar 

  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 272:159–163

    Article  CAS  Google Scholar 

  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 49:2289–2293

    Article  CAS  Google Scholar 

  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 2683–2686

    Google Scholar 

  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 274:109–115

    Article  CAS  Google Scholar 

  55. Kobayashi S, Manabe K (2002) Development of novel Lewis acid catalysts for selective organic reactions in aqueous media. Acc Chem Res 35:209–217

    Article  CAS  Google Scholar 

  56. Azoulay S, Manabe K, Kobayashi S (2005) Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water. Org Lett 7:4593–4595

    Article  CAS  Google Scholar 

  57. Ogawa C, Azoulay S, Kobayashi S (2005) Bismuth triflate-chiral bipyridine complex catalyzed asymmetric ring opening reactions of meso-epoxide in water. Heterocycles 66:201–206

    Article  CAS  Google Scholar 

  58. Schneider C, Sreekanth AR, Mai E (2004) Scandium-bipyridine-catalyzed enantioselective addition of alcohols and amines to meso-epoxides. Angew Chem Int Ed 43:5691–5694

    Article  CAS  Google Scholar 

  59. Tschöp A, Marx A, Sreekanth AR, Schneider C (2007) Scandium-bipyridine-catalyzed enantioselective alcoholysis of meso-epoxides. Eur J Org Chem 2007:2318–2327

    Article  Google Scholar 

  60. Bonollo S, Fringuelli F, Pizzo F, Vaccaro L (2008) Zn(II)-catalyzed desymmetrization of meso-epoxides by aromatic amines in water. Synlett 1574–1578

    Google Scholar 

  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 66:1111–1118

    Article  CAS  Google Scholar 

  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 348:2585–2589

    Article  CAS  Google Scholar 

  63. Iranpoor N, Firouzabadi H, Shekarize M (2003) Micellar media for the efficient ring opening of epoxides with CN, N 3 , NO 3 , NO 2 , SCN, Cl and Br catalyzed with Ce(OTf)4. Org Biomol Chem 1:724–727

    Article  CAS  Google Scholar 

  64. (a) Patai S (1971) The Chemistry of the azido group. Wiley, New York; (b) Scriven EFV, Turnbull K (1988) Chem Rev 88:297–368

    Google Scholar 

  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 9:2063–2067

    Article  CAS  Google Scholar 

  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 73:8382–8385

    Article  CAS  Google Scholar 

  67. Various Authors (1999) The chemistry and biology of β-amino acids. In: Hoekstra WJ (ed) Curr Med Chem 6:905–1002

    Google Scholar 

  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 331:87–89

    Article  CAS  Google Scholar 

  69. Juaristi E (1997) Enantioselective synthesis of β-amino acids. Wiley-VCH, New York

    Google Scholar 

  70. Cardillo G, Tomasini C (1996) Asymmetric synthesis of ß-amino acids and α-substituted β-amino acids. Chem Soc Rev 25:117–127

    Article  CAS  Google Scholar 

  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 48:13409–13422

    Article  Google Scholar 

  72. Legters J, Thijs L, Zwanenburg B (1992) A convenient synthesis of aziridine-2-carboxylic esters. Recl Trav Chim Pays-Bas 111:1–23

    Article  CAS  Google Scholar 

  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 50:1560–1563

    Article  CAS  Google Scholar 

  74. Fringuelli F, Pizzo F, Vaccaro L (2000) Cobalt(II) chloride-catalyzed chemoselective sodium borohydride reduction of azides in water. Synthesis 646–650

    Google Scholar 

  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 93:405–413

    Article  CAS  Google Scholar 

  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 10:4261–4264

    Article  CAS  Google Scholar 

  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 2:247–250

    Article  Google Scholar 

  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 352:2489–2496

    Google Scholar 

  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 15:12255–12262

    Article  CAS  Google Scholar 

  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 1392–1402

    Google Scholar 

  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 45:1309–1312

    Article  CAS  Google Scholar 

  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 42:6625–6627

    Article  Google Scholar 

  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 9:3647–3650

    Article  CAS  Google Scholar 

  84. Roelfes G, Boersma A J, Feringa B L (2006) Highly enantioselective DNA-based catalysis. Chem Commun 635–637

    Google Scholar 

  85. Roelfes G, Feringa BL (2005) DNA-based asymmetric catalysis. Angew Chem Int Ed 44:3230–3232

    Article  CAS  Google Scholar 

  86. Dijk EW, Feringa BL, Roelfes G (2008) DNA-based hydrolytic kinetic resolution of epoxides. Tetrahedron Asymmetry 19:2374–2377

    Article  CAS  Google Scholar 

  87. van der Werf MJ, Jongejan H, Franssen MCR (2001) Resolution of limonene 1,2-epoxide diastereomers by mercury(II) ions. Tetrahedron Lett 42:5521–5524

    Article  Google Scholar 

  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 43:3237–3238

    Article  Google Scholar 

  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 68:9119–9121

    Article  CAS  Google Scholar 

  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 67:4599–4601

    Article  CAS  Google Scholar 

  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 10:4129–4142

    Article  CAS  Google Scholar 

  92. Justo De Pomar JC, Soderquist A (1998) Regio- and stereospecific synthesis of (O-TIPS)-protected 2-hydroxyalkylmercaptans from epoxides and triisopropylsilanethiol. Tetrahedron Lett 39:4409–4412

    Article  CAS  Google Scholar 

  93. Yamada O, Ogasawara K, Synlett 427–428

    Google Scholar 

  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 50:5696–5704

    Article  CAS  Google Scholar 

  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 29:582–584

    Article  CAS  Google Scholar 

  96. Smith MB, March MB (2001) March’s advanced organic chemistry, 5th edn. Wiley-Interscience Publication, New York

    Google Scholar 

  97. Streitwieser A (1952) Solvolytic displacement reactions at saturated carbon atoms. Chem Rev 56:571, cfr. page 582

    Article  Google Scholar 

  98. Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L (2005) Thiolysis of 1,2-epoxides under environmentally friendly conditions. Targets Heterocycl Syst 8:147–161

    Google Scholar 

  99. Lauret C (2001) Epoxy ketones as versatile building blocks in organic synthesis. Tetrahedron Asymmetry Rep N 52(12):2359–2383

    Article  Google Scholar 

  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 8:191–196

    Article  CAS  Google Scholar 

  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 69:7745–7747

    Article  CAS  Google Scholar 

  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 50:5009–5011

    Article  Google Scholar 

  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 7:43–45

    Article  CAS  Google Scholar 

  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 20:1025–1029

    Article  CAS  Google Scholar 

  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 9:1497–1500

    Article  CAS  Google Scholar 

  106. Gao P, Xu P-F, Zhai H (2008) Borax-catalyzed thiolysis of 1,2-epoxides in aqueous medium. Tetrahedron Lett 49:6536–6538

    Article  CAS  Google Scholar 

  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 38:904–905

    Article  CAS  Google Scholar 

  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 261:1–5

    Article  CAS  Google Scholar 

  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 46:8837–8839

    Article  CAS  Google Scholar 

  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 44:5323–5326

    Article  Google Scholar 

  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 11:541–545

    Article  CAS  Google Scholar 

  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 133:161–166

    Article  CAS  Google Scholar 

  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 64:1884–1888

    Article  CAS  Google Scholar 

  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 797–798

    Article  CAS  Google Scholar 

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Acknowledgments

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.

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Correspondence to Luigi Vaccaro .

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© 2012 Springer Science+Business Media B.V.

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Lanari, D., Piermatti, O., Pizzo, F., Vaccaro, L. (2012). Water as Reaction Medium in the Synthetic Processes Involving Epoxides. In: Mohammad, A. (eds) Green Solvents I. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-1712-1_7

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