Additive‐Free Thiolysis of Epoxides in Water: A Green and Efficient Regioselective Pathway to β‐Hydroxy Sulfides

References

• Wasserscheid , P. and Welton , T. 2003 . Ionic Liquids in Synthesis Weinheim, , Germany : Wiley‐VCH .
   Google Scholar
• Yadav , J. S. , Reddy , B. V. S. , Eshwaraiah , B. , Srinivas , M. and Vishnumurthy , P. 2003 . Three‐component coupling reactions in ionic liquids: a facile synthesis of α‐aminonitriles . New J. Chem. , 27 : 462 – 465 .
   Web of Science ®Google Scholar
• Kaupp , G. 1994 . Reactions in supercritical carbon dioxide . Angew. Chem., Int. Ed. Engl. , 33 : 1452 – 1455 .
   Web of Science ®Google Scholar
• Cornils , B. and Hermann , W. A. 1998 . Aqueous‐Phase Organometallic Catalysis Weinheim, , Germany : Wiley‐VCH .
   Google Scholar
• Li , C. J. and Chan , T. H. 1997 . Organic Reactions in Aqueous Media New York : John Wiley & Sons .
   Google Scholar
• Li , C. J. 2005 . Organic reactions in aqueous media with a focus on carbon–carbon bond formations: a decade update . Chem. Rev. , 105 : 3095 – 3166 .
   PubMed 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 – 1616 .
   PubMed Web of Science ®Google Scholar
• Amantini , D. , Fringuelli , F. , Piermatti , O. and Vaccaro , L. 2002 . Nucleophilic ring opening of 1,2‐epoxides in aqueous medium . Arkivoc , : 293 – 311 .
   Google Scholar
• Corey , E. J. , Clark , D. A. , Goto , G. , Marfat , A. , Mioskowski , C. , Samuelsson , B. and Hammarstrom , S. 1980 . Additions and corrections—Stereospecific total synthesis of a “slow reacting substance” of anaphylaxis leukotriene C‐1 . J. Am. Chem. Soc. , 102 : 3663 – 3363 .
   Google Scholar
• Corey , E. J. , Clark , D. A. and Goto , G. 1980 . Total synthesis of slow reacting substances (SRS): “Leukotriene C‐2” (11 trans leukotriene C) (3) and leukotriene D (4) . Tetrahedron Lett. , 21 : 3143 – 3146 .
   Web of Science ®Google Scholar
• Hammarstrom , S. , Samuelsson , B. , Clark , D. A. , Goto , G. , Marfat , A. , Mioskowski , C. and Corey , E. J. 1980 . Stereochemistry of leukotriene C‐1 . Biochem. Biophys. Res. Commum. , 92 : 946 – 953 .
   PubMed Web of Science ®Google Scholar
• Corey , E. J. , Clark , D. A. , Goto , G. , Marfat , A. , Mioskowski , C. , Samuelsson , B. and Hammarstrom , S. 1980 . Stereospecific total synthesis of a “slow reacting substance” of anaphylaxis, leukotriene C‐1 . J. Am. Chem. Soc. , 102 : 1436 – 1439 .
   Web of Science ®Google Scholar
• Kesavan , V. , Bonnet‐Delphon , D. and Begue , J. P. 2000 . Fluoro alcohol as reaction medium: one‐pot synthesis of β‐hydroxy sulfoxides from epoxides . Tetrahedron Lett. , 40 : 2895 – 2898 . and references cited therein
   Web of Science ®Google Scholar
• Begue , J. P. , Bonnet‐Delphon , D. and Kornilov , A. 1996 . Synthesis of 3‐(alkylthio and phenylthio)‐1,1,1‐trifluoroalkan‐2‐ones via ring opening of epoxy ethers . Synthesis , : 529 – 532 .
   Google Scholar
• Ranu , B. C. and Mandal , T. 2006 . Indium(I) iodide promoted cleavage of dialkyl disulfides—Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides . Can. J. Chem. , : 762 – 770 .
   Web of Science ®Google Scholar
• Chandrasekhar , S. , Reddy , C. R. , Babu , B. N. and Chandrashekar , G. 2002 . Highly efficient cleavage of epoxides catalyzed by B(C6F5)3 . Tetrahedron Lett. , 43 : 3801 – 3803 .
   Web of Science ®Google Scholar
• Cossy , J. , Bellosta , V. , Alauze , V. and Desmurs , J. R. 2002 . Lithium bistrifluoromethanesulfonimidate‐mediated regioselective ring opening of aziridines by amines . Synthesis , : 2211 – 2214 .
   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, benzeneselenol, amines, and acetic acid . J. Am. Chem. Soc. , 99 : 8208 – 8214 .
   Web of Science ®Google Scholar
• Iida , T. , Yamamoto , N. , Sasai , H. and Shibasaki , M. 1997 . A highly enantioselective ring opening of epoxides with thiols catalyzed by a gallium·lithium·bis(binaphthoxide) complex . J. Am. Chem. Soc. , 119 : 4783 – 4784 .
   Web of Science ®Google Scholar
• Polshettiwar , V. and Kaushik , M. P. 2004 . CsF–Celite catalyzed regio‐ and chemoselective SN2 type ring opening of epoxides with thiol . Catal. Commun. , 5 : 515 – 518 .
   Web of Science ®Google Scholar
• Yadav , J. S. , Reddy , B. V. S. and Baishya , G. 2002 . InCl3‐catalyzed highly regioselective ring opening of epoxides with thiols . Chem. Lett. , : 906 – 907 .
   Web of Science ®Google Scholar
• Chini , M. , Crotti , P. , Giovani , E. , Macchia , F. and Pineschi , M. 1992 . Stereo‐ and regioselective metal salt‐promoted ring opening of 1,2‐epoxides with thiols in acetonitrile . Synlett , : 303 – 305 .
   Google Scholar
• Fringuelli , F. , Pizzo , F. , Tortoioli , S. and Vaccaro , L. 2003 . Thiolysis of 1,2‐epoxides by thiophenol catalyzed under solvent‐free conditions . Tetrahedron Lett. , 44 : 6785 – 6787 .
   Web of Science ®Google Scholar
• Cossy , J. , Bellosta , V. , Hamior , C. and Desmurs , J. R. 2002 . Regioselective ring opening of epoxides by nucleophiles mediated by lithium bistrifluoromethanesulfonimide . Tetrahedron Lett. , 43 : 7083 – 7086 .
   Web of Science ®Google Scholar
• Firouzabadi , H. , Iranpoor , N. , Jafari , A. A. and Makarem , S. 2006 . Aluminumdodecatungstophosphate (AlPW12O40) as a reusable Lewis acid catalyst: Facile regioselective ring opening of epoxides with alcohols, acetic acid and thiols . J. Mol. Catal. A: Chem. , 250 : 237 – 242 .
   Web of Science ®Google Scholar
• Fringuelli , F. , Pizzo , F. , Tortoioli , S. and Vaccaro , L. 2002 . Thiolysis of alkyl‐ and aryl‐1,2‐epoxides in water catalyzed by InCl3 . Adv. Synth. Catal. , 344 : 379 – 384 .
   Web of Science ®Google Scholar
• Amantini , D. , Fringuelli , F. , Pizzo , F. , Tortoioli , S. and 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
• Fringuelli , F. , Pizzo , F. , Tortoioli , S. and Vaccaro , L. 2003 . Easy and environmentally friendly uncatalyzed synthesis of beta‐hydroxy arylsulfides by thiolysis of 1,2‐epoxides in water . Green Chem. , 5 : 436 – 440 .
   Web of Science ®Google Scholar
• Fringuelli , F. , Pizzo , F. , Tortoioli , S. and Vaccaro , L. 2003 . Zn(II)‐catalyzed thiolysis of oxiranes in water under neutral conditions . J. Org. Chem. , 68 : 8248 – 8251 .
   PubMed Web of Science ®Google Scholar
• Reddy , M. S. , Srinivas , B. , Srindhar , R. , Narender , M. and Rao , K. R. 2006 . Highly regioselective thiolysis of oxiranes under supramolecular catalysis involving β‐cyclodextrin in water . J. Mol. Catal. A: Chem. , 255 : 180 – 183 .
   Web of Science ®Google Scholar
• Wu , J. and 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 beta‐amino alcohols and beta‐aminothioethers . Green Chem. , 7 : 708 – 710 .
   Web of Science ®Google Scholar
• Pironti , V. and Colonna , S. 2005 . Microwave‐promoted synthesis of beta‐hydroxy sulfides and beta‐hydroxy sulfoxides in water . Green Chem. , 7 : 43 – 45 .
   Web of Science ®Google Scholar
• Mojtahedi , M. M. , Abbasi , H. , Abaee , M. S. and Mohebali , B. 2006 . Solvent‐free thiolysis of epoxides under lithium perchlorate catalysis . Monatsh. Chem. , 137 : 455 – 458 .
   Web of Science ®Google Scholar
• Mojtahedi , M. M. , Ghasemi , H. , Abaee , M. S. and Bolourtchian , M. 2005 . Microwave‐assisted ring opening of epoxides with thiols on montmorillonite K‐10 solid support . Arkivoc , : 68 – 73 .
   Web of Science ®Google Scholar
• Mojtahedi , M. M. , Abaee , M. S. , Bolourtchian , M. and Abbasi , H. 2007 . Facile room temperature MgBr2 · OEt2 catalyzed thiolysis of epoxides under solvent‐free conditions . Phosphorus Sulfur Relat. Elem. , 182 : 905 – 910 .
   Web of Science ®Google Scholar
• Mojtahedi , M. M. , Abaee , M. S. , Heravi , M. M. and Behbahani , F. K. 2007 . Additive‐free chemoselective acylation of amines and thiols . Monatsh. Chem. , 138 : 95 – 99 .
   Web of Science ®Google Scholar
• Schreiner , P. R. 2003 . Metal‐free organocatalysis through explicit hydrogen bonding interactions . Chem. Soc. Rev. , 32 : 289 – 296 . and references cited therein. For H‐bonded catalyzed reactions, see. For H‐bonded catalyzed reactions, see
   PubMed Web of Science ®Google Scholar