Journal of the American Chemical Society

Synthesis of. beta.-acylacrylic esters and. alpha.,. beta.-butenolides via. beta.-keto sulfoxide alkylation

PA Bartlett

Index: Bartlett,P.A. Journal of the American Chemical Society, 1976 , vol. 98, # 11 p. 3305 - 3312

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Citation Number: 43

Abstract

Abstract: Alkylation of the anions derived from (methylsulfinyl) methyl ketones (1) with methyl bromoacetate proceeds readily to afford the 3-(methylsulfinyl)-4-oxobutanoates (2). These intermediates are converted to the corresponding unsaturated keto esters (3) in excellent overall yield (Table I) by thermal elimination of methylsulfenic acid. Alternatively, the y-sub- stituted-Lu, P-butenolides (5) are obtained on sodium borohydride reduction of the ...