Selective. gamma.-substitution of. alpha.,. beta.-unsaturated esters via. alpha.-trimethylsilyl. beta.,. gamma.-unsaturated esters

P Albaugh-Robertson…

Index: Albaugh-Robertson, Pamela; Katzenellenbogen, John A. Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5288 - 5302

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Citation Number: 33

Abstract

In order to achieve selective y-substitution of a $-unsaturated esters, we investigated the directive effect of silicon in the reaction of various electrophiles with a-trimethylsilyl P, y- unsaturated esters. These esters were prepared by nickel-catalyzed vinylation reactions of the lithium enolate of ethyl a-(trimethylsily1) acetate. The a-silyl P, y-unsaturated esters reacted with a variety of electrophiles (aldehydes, ketones, acetals, ketals, acid chlorides, ...