The reaction of dialkylcopper lithium reagents with 3-halo-2-acylaminoacrylic acids

KD Richards, AJ Kolar, A Srinivasan…

Index: Richards,K.D. et al. Journal of Organic Chemistry, 1976 , vol. 41, p. 3674 - 3677

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Citation Number: 14

Abstract

Reaction of (Z)-3-bromo-2-(2-phenylacetamido) acrylic acid (1) with MezCuLi yielded (Z)-2- (2-phenylacetamido) crotonic acid (3), while the reaction with n-BuzCuLi gave a 2: l mixture of 2 and E isomers, 5 and 6, of 2-(2-phenylacetamido) hept-2-enoic acid. In each case, the reduction product, 2-(2-phenylacetamido) acrylic acid (4), was formed as a minor product. The (2)-3-~ hloroacrylate 7, upon reaction with MezCuLi, gave the (2)-crotonate 8, while a ...