A new way toward Z. alpha.,. beta. unsaturated esters: a pyrethroid application

…, JP Demoute, P Dutheil, I Terrie, J Tessier

Index: Babin, Didier; Demassey, Jacques; Demoute, Jean Pierre; Dutheil, Phillipe; Terrie, Isabelle; Tessier, Jean Journal of Organic Chemistry, 1992 , vol. 57, # 2 p. 584 - 589

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Citation Number: 13

Abstract

Use of the stereospecific condensation of,!? carbalkoxysulfones with aldehydes, followed by the stereospecific reduction of the afforded sulfonyl acrylate with sodium dithionite allows us to propose this method as a new way to prepare 2 a,@ unsaturated esters. Steric hindrance seems to be the reason for the selectivity of the reduction and the mechanism was proved, by X-ray of an intermediate, to be a cis Michael addition of HS02-, followed by an anti ...