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Synlett 2003(3): 0365-0368
DOI: 10.1055/s-2003-37105
DOI: 10.1055/s-2003-37105
LETTER
© Georg Thieme Verlag Stuttgart · New York
Enantiopure Guanidine Bases For Enantioselective Enone Epoxidations: 1, Acyclic Guanidines
Further Information
Publication History
Received
20 December 2002
Publication Date:
07 February 2003 (online)


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%.
Key words
enantioselective - epoxidation - enones - guanidines - stereoselectivity