Synthesis of allylcarboxylic acids from olefins with diethyl oxomalonate, an enophilic equivalent of carbon dioxide

MF Salomon, SN Pardo…

Index: Salomon, Mary F.; Pardo, Simon N.; Salomon, Robert G. Journal of the American Chemical Society, 1980 , vol. 102, # 7 p. 2473 - 2475

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Citation Number: 35

Abstract

Control of the sites of CC bond formation and CH bond cleavage is important for synthetic exploitation of allylic activation in carbon skeletal construction. Ene reactions' of diethyl oxomalonate*(2), constrained by a pericyclic mechanism to occur with allylic transposition of the C= C bond, substitute an a-hydroxymalonyl group for allylic hydrogen (1+ 3). Conversion of this group into carboxyl allows olefin functionalization equivalent to an ene reaction of ...