2003•SynlettRequires access

Enantiopure Guanidine Bases For Enantioselective Enone Epoxidations: 1, Acyclic Guanidines

Richard J. K. Taylor, Julie C. McManus, John Carey

Abstract

A range of structurally and functionally varied enantiopure guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tert-butoxycarbonylamino-4,4-dimethoxycyclohexa-2,5-dien-1-one 1 using tert-butylhydroperoxide. Successful enantioselective epoxidations were observed and useful structure-activity data obtained, but the reactions were slow and the maximum ee observed was 30%.

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Key concepts: Enantiopure drug, Enantioselective synthesis, Chemistry, Guanidine, Enone, Stereochemistry, Organic chemistry, Catalysis