Synlett 2003(3): 0365-0368
DOI: 10.1055/s-2003-37105
LETTER
© Georg Thieme Verlag Stuttgart · New York

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

Julie C. McManusa, John S. Careyb, Richard J. K. Taylor*a
a Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
Fax: +44(1904)434523; e-Mail: rjkt1@york.ac.uk;
b GlaxoSmithKline Pharmaceuticals, Leigh, Tonbridge, Kent TN11 9AN, UK
Further Information

Publication History

Received 20 December 2002
Publication Date:
07 February 2003 (online)

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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%.