Palladium-catalyzed 1, 3-oxygen-to-carbon alkyl shifts. Basic studies

BM Trost, TA Runge

Index: Trost,B.M.; Runge,T.A. Journal of the American Chemical Society, 1981 , vol. 103, p. 7550

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Citation Number: 55

Abstract

Abstract:[l-(Carbomethoxy) alkylidene]-5-vinyltetrahydrofurans which arise from preferential 0-alkylation upon cyclization of@-keto esters smoothly rearrange to the desired C-alkylation products, 2-(carbomethoxy)-3-~ inylcyclopentanones, with catalysis by Pd (0). With the methyl-substituted analogue, Le., 2-(5-vinyltetrahydrofuran-2-ylidene) propionate, the major product is (Z)-2-(carbomethoxy)-2-methyl-3-vinylcyclopentanone. On the other hand, 1-( ...