Catalytic Enantioselective Conversion of Epoxides to Thiiranes

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• 作者：Saihu Liao ; Markus Leutzsch ; Mattia Riccardo Monaco ; Benjamin List
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：April 27, 2016
• 年：2016
• 卷：138
• 期：16
• 页码：5230-5233
• 全文大小：368K
• 年卷期：0
• ISSN：1520-5126

文摘

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 %.