Catalytic Enantioselective Conversion of Epoxides to Thiiranes.

Liao, Saihu; Leutzsch, Markus; Monaco, Mattia Ricardo; List, Benjamin

doi:10.1021/jacs.6b01960

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Catalytic Enantioselective Conversion of Epoxides to Thiiranes.

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Liao, Saihu
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch, Markus
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Monaco, Mattia Ricardo
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Liao, S., Leutzsch, M., Monaco, M. R., & List, B. (2016). Catalytic Enantioselective Conversion of Epoxides to Thiiranes. Journal of the American Chemical Society, 138(16), 5230-5233. doi:10.1021/jacs.6b01960.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002A-4A4F-0

Abstract

A highly efficient and enantioselective Brønsted acid catalyzed conversion of epoxides to thiiranes has been developed. The reaction proceeds in a kinetic resolution, furnishing both epoxide and thiirane in high yields and enantiomeric purity. Heterodimer formation between the catalyst and sulfur donor affords an effective way to prevent catalyst decomposition and enables catalyst loadings as low as 0.01 mol %.