Lewis acid induced conjugate addition of alkenes to. alpha.,. beta.-unsaturated ketones or aldehydes

BB Snider, DJ Rodini, J Van Straten

Index: Snider,B.B.; Rodini,D.J.; Straten,J.V. Journal of the American Chemical Society, 1980 , vol. 102, p. 5872

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Citation Number: 71

Abstract

Abstract: a,@-Unsaturated ketones or aldehydes form a 1: 2 complex with ethylaluminum dichloride which reacts with alkenes either intermolecularly or intramolecularly to give a zwitterion. The zwitterion collapses reversibly to a cyclobutane in geometrically favorable cases and undergoes hydride and alkyl shifts to generate a,@-unsaturated carbonyl compounds. The intramolecular reactions proceed with high regia-and stereospecificity ( ...