Stereoselective alkene synthesis via (. alpha.-chloroalkyl)(dimethyl) phenylsilanes and. alpha.-(dimethyl) phenylsilyl ketones

AGM Barrett, JM Hill, EM Wallace

Index: Barrett, Anthony G. M.; Hill, Jason M.; Wallace, Eli M. Journal of Organic Chemistry, 1992 , vol. 57, # 1 p. 386 - 389

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Citation Number: 28

Abstract

Introduction The acid or base elimination of a diastereoisomerically pure &hydroxy silane 1 (the Peterson olefination reaction') provides one of the very best methods for the stereoselective formation of alkenes. Either the E or Z isomer may be prepared with excellent geometric selectivity from a single precursor (Scheme I). Thus, elimination of the syn diastereoisomer 1 under basic conditions proceeds via a syn manifold and the ...