Synthesis

Formation of β-substituted γ-keto esters via zinc carbenoid mediated chain extension

W Lin, RJ McGinness, EC Wilson, CK Zercher

Index: Lin, Weimin; McGinness, Robert J.; Wilson, Emerald C.; Zercher, Charles K. Synthesis, 2007 , # 15 p. 2404 - 2408

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Citation Number: 5

Abstract

Chain-extension reactions based upon the intermediacy of donor-acceptor cyclopropanes have been used to prepare a variety of γ-dicarbonyl species. [1] In this vein, a one-step zinc carbenoid mediated chain-extension reaction has been developed in our laboratories in which β-keto esters 1 can be transformed into γ-keto carbonyls through application of the Furukawa modification of the Simmons-Smith reagent. [2] A proposed mechanism (Scheme [1] ) for the chain ...