Synlett

A stereoselective synthesis of trans-1, 2-disubstituted alkenes based on the condensation of aldehydes with metallated 1-phenyl-1H-tetrazol-5-yl sulfones

PR Blakemore, WJ Cole, PJ Kocieński, A Morley

Index: Blakemore, Paul R.; Cole, William J.; Kocienski, Philip J.; Morley, Andrew Synlett, 1998 , # 1 p. 26 - 28

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Citation Number: 349

Abstract

In 1991 Sylvestre Julia and co-workers1 reported a new connective one- pot synthesis of alkenes involving the reaction of lithiated 2- benzothiazolyl sulfones with carbonyl compounds (Scheme 1). The reaction involves addition of carbanion 1 to the carbonyl compound to give adduct 2 which then undergoes a series of transformations resulting in the expulsion of sulfur dioxide and the lithium derivative of 1,3- benzothiazol-2-one (5) with concomitant formation of the alkene. ...