Asymmetric nucleophilic ring opening of meso-epoxides is a powerful method to synthesize chiral 1,2 functionalized organic compounds. Nucleophiles such as amines, azides, alcohols and cyanides have been extensively investigated for this reaction. However, there are only few reports on epoxide ring opening with thiols. Additionally, the catalysts used for this transformation were mostly limited the chiral BINOL /salen metal complexes. Chiral BINOL phosphate salts were recently shown to catalyze a number of reactions involving imine and oxyindole substrates. We have developed a first example of desymmterization of meso-epoxides with thiols using chiral BINOL phosphate salts. The reaction provided the �-hydroxy sulfides in excellent yield and enantioselectivity. The wide range of epoxides and thiols were excellent substrates for this reaction.

Desymmetrization of <i>meso-</i>epoxides with thiols catalyzed by BINOL phosphate salts

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Desymmetrization of meso-epoxides with thiols catalyzed by BINOL phosphate salts