Stereospecific formation of enolates from reaction of unsymmetrical ketenes and organolithium reagents

LM Baigrie, HR Seiklay, TT Tidwell

Index: Baigrie,L.M.; Seiklay,H.R.; Tidwell,T.T. Journal of the American Chemical Society, 1985 , vol. 107, p. 5391

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Citation Number: 86

Abstract

Abstract: Reaction of unsymmetrical ketenes RR'C= C= O (4, R, R'= CMe,(CH,),; 8, R= Ph, R'= Me; 9, R= Ph, R'= Et; 10, R= Me3%, R'= Et; 11, R= t-Bu, R'= H) with organolithiums R” Li (R”= n-Bu, Ph, t-Bu, CH2= CH, HCEC) followed by silylation with Me3SiC1 gave stereospecific formation of a single silyl enol ether in each case. This result is interpreted in terms of preferential attack by the organolithium reagent in the plane of the ketene from ...