Regioselective Reaction of Epoxides with Disulfides Using Zn/AlCl₃ System: A Simple Synthesis of β-Hydroxy Sulfides

References

• Roush , W.R. and Brown , B.B. 1992 . Enantioselective synthesis of 2-Alkyl-5-methylene-1,3-dioxolan-4-ones and exo-selective Diels–Alder reactions with cyclopentadiene . J. Org. Chem. , 57 : 3380
   Web of Science ®Google Scholar
• Kim , M.J. and Choi , Y.K. 1992 . Lipase-catalyzed enantioselective transesterification of O-trityl 1,2-diols. Practical synthesis of (R)-tritylglycidol . J. Org. Chem. , 57 : 1605
   Web of Science ®Google Scholar
• Guivisdalsky , P.N. and Bittman , R. 1989 . Glycidyl derivatives as chiral C3 synthons. Ring opening catalyzed by BF3 etherate . J. Am. Chem. Soc. , 111 : 3077
   Web of Science ®Google Scholar
• Bortolini , O. , DiFuria , F. , Licini , G. and Modena , G. 1988 . Asymmetric oxidation of β-hydroxy sulfides. The role of the hydroxy group . Phosphorous Sulfur , 37 : 171
   Web of Science ®Google Scholar
• Ko , S.Y. , Masamune , H. and Sharpless , K.B. 1987 . Nitrobenzoate esters of epoxy alcohols: Convenient synthons for water-soluble epoxy alcohols . J. Org. Chem. , 52 : 667
   Web of Science ®Google Scholar
• Luly , J.R. , Yi , N. , Soderquist , J. , Stein , H. , Cohen , J. , Perun , T.J. and Plattner , J.J. 1987 . New inhibitors of human renin that contain novel Leu-Val replacements . J. Med. Chem. , 30 : 1609
   PubMed Web of Science ®Google Scholar
• Chini , M. , Crotti , P. , Giovani , E. , Macchina , F. and Pineschi , M. 1992 . Stereo- and regioselective metal salt-promoted ring opening of 1,2-epoxides with thiols in acetonitrile . Synlett. , : 303
   Web of Science ®Google Scholar
• Meffe , P. , Quang , L. Vo. , Quang , Y. Vo. and Le Goffic , F. 1990 . Unusual α-aminoacids from vinylglycine . Tetrahedron Lett. , 31 : 2291
   Web of Science ®Google Scholar
• Vougioukas , A.E. and Kagan , B.H. 1987 . Oxirane ring opening reactions with thiols catalyzed by lanthanide complexes . Tetrahedron Lett. , 28 : 6065
   Web of Science ®Google Scholar
• Iqbal , J. , Panday , A. , Shukla , A. , Srivastava , R.R. and Tripathi , S. 1990 . Cobalt mediated regioselective ring opening of oxiranes with benzenethiol: A mechanistic study . Tetrahedron. , 46 : 6423
   Web of Science ®Google Scholar
• Posner , G.H. and Rogers , D.Z. 1977 . Organic reactions at alumina surfaces. Mild and selective opening of epoxides by alcohols, thiols, benzeneselenole, amines, and acetic acid . J. Am. Chem. Soc. , 99 : 8208
   Web of Science ®Google Scholar
• Iizawa , T. , Goto , A. and Nishikubo , T. 1989 . Regioselective reaction of oxiranes with S-phenyl thioesters catalyzed by quaternary onium or crown ether–metal salt complexes . Bull. Chem. Soc. Jpn. , 62 : 597
   Web of Science ®Google Scholar
• Nishikubo , T. , Iizawa , T. , Shimojo , M. , Kato , T. and Shiina , A. 1990 . New catalytic activity of polymer-supported quaternary onium salts. Regioselective addition reaction of oxiranes with active esters catalysed by insoluble polystyrene-bound quaternary ammonium and phosphorium salts . J. Org. Chem. , 55 : 2536
   Web of Science ®Google Scholar
• Albanese , D. , Landini , D. and Penso , M. 1994 . Tetrabutylammonium fluoride: A powerful catalyst for the regioselective opening of epoxides with thiols . Synthesis , : 34
   Web of Science ®Google Scholar
• Maiti , A.K. , Biswas , G.K. and Bhattacharyya , P. 1993 . Montmorillonite clay-catalysed regioselective ring opening of oxiranes with thiophenol: A simple synthesis of β-hydroxy sulfides . J. Chem. Res. (S) , : 325
   Web of Science ®Google Scholar
• Biswas , G.K. and Bhattacharyya , P. 1991 . Regioselective ring opening of oxiranes catalysed by montmorillonite clay: A simple synthesis of β-hydroxy sulfones . Synth. Commun. , 21 : 569
   Web of Science ®Google Scholar
• Iranpoor , N. , Baltork , I.M. and Zardaloo , F.S. 1991 . Ceric ammonium nitrate. An efficient catalyst for mild and selective opening of epoxides in the presence of water, thiols and acetic acid . Tetrahedron. , 47 : 9861
   Web of Science ®Google Scholar
• Still , I.W. and Martyn , L.J.P. 1998 . The generation of (Samarium) thiolates from aryl thiocyanates and their reaction with epoxides. A route to β-hydroxy sulfides . Synth. Commun. , 28 : 913
   Web of Science ®Google Scholar
• Movassagh , B. , Lakouraj , M.M. and Fadaei , Z. 2000 . Synthesis of organic sulfides from disulfides using a Zn/AlCl3 system in aqueous media . J. Chem. Res. (S) , : 350
   Web of Science ®Google Scholar
• 2001 . A convenient one-pot synthesis of thiol esters from disulfides using a Zn/AlCl3 system . J. Chem. Res. (S) , : 22
   Web of Science ®Google Scholar
• Lakouraj , M.M. , Movassagh , B. and Fadaei , Z. 2002 . Synthesis of organic sulfides via Zn/AlCl3 system in aqueous media . Synth. Commun. , 32 : 1237
   Web of Science ®Google Scholar
• Lakouraj , M.M. , Movassagh , B. and Fadaei , Z. 2001 . Convenient synthesis of thiol esters from acyl chlorides and disulfides using Zn/AlCl3 . Monatsh. Chem. , : 1
   Web of Science ®Google Scholar
• Jia , X. , Zhang , Y. and Zhou , X. 1994 . Reductive cleavage of S–S bond in diphenyl disulfide by samarium diiodide: A novel method for the synthesis of thiol esters . Synth. Commun. , 24 : 387
   Web of Science ®Google Scholar
• Movassagh , B. , Lakouraj , M.M. and Ghodrati , K. 1999 . Caro's acid supported on silica gel. Part 1: Oxidative coupling of thiols to disulfides . Synth. Commun. , 29 : 3597
   Web of Science ®Google Scholar