Stereoselective and regioselective Lewis acid catalyzed ene reactions of. alpha.-substituted acrylate esters

JV Duncia, PT Lansbury Jr, T Miller…

Index: Duncia,J.V.; Lansbury,P.T.; Miller,T. Journal of the American Chemical Society, 1982 , vol. 104, p. 1930

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Citation Number: 21

Abstract

Abstract: EtAlCl, catalyzes the ene reactions of a-substituted acrylate esters with trans 1, 2-di- and trisubstituted alkenes at 25 OC. The reactions are regio-and stereoselective. The ester group adds endo and a hydrogen is transferred selectively from the alkyl group syn to the vinylic hydrogen. Methyl a-chloroacrylate, a-bromoacrylate, acetamidoacrylate, and methacrylate, ethyl a-bromomethylacrylate, and dimethyl itaconate were explored. Ene ...