Organic letters

Facile Synthesis of cis-2-Alkyl-3-trialkylsilyloxycycloalkanones via the Non-Aldol Aldol Rearrangement of 2, 3-Epoxycycloalkanols

ME Jung, DA Allen

Index: Jung, Michael E.; Allen, Damian A. Organic Letters, 2008 , vol. 10, # 10 p. 2039 - 2041

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Citation Number: 11

Abstract

Silyl triflate-promoted rearrangement of cis-2, 3-epoxycycloalkanols A, prepared by epoxidation of the cyclic allylic alcohol and then silylation, afforded good yields (∼ 70–75%) of the cis-2-alkyl-3-silyloxycycloalkanones B, presumably via the intermediates C and D, even with quite large α-substituents, eg, tert-butyl. Finally, it has been shown that the stereochemistry of the epoxy alcohol is crucial as one would expect from the mechanism.

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