Alkylation of ketene silyl acetals with nitroolefins mediated by sterically encumbered Lewis acids

JA Tucker, TL Clayton, DM Mordas

Index: Tucker, John A.; Clayton, Terrance L.; Mordas, Donald M. Journal of Organic Chemistry, 1997 , vol. 62, # 13 p. 4370 - 4375

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Citation Number: 14

Abstract

The utility of nitroolefins as “+ CC-NH2” and “+ C (CO) R” synthons is limited by their facile polymerization in the presence of nucleophiles. Although a number of procedures have been developed for the successful alkylation of ketones with nitroolefins, currently available procedures for the corresponding reaction of esters suffer from important limitations such as modest yields, lack of demonstrated generality, inconveniently low reaction temperatures, ...