Chemical Communications

Catalytic amide formation with α′-hydroxyenones as acylating reagents

PC Chiang, Y Kim, JW Bode

Index: Chiang, Pei-Chen; Kim, Yoonjoo; Bode, Jeffrey W. Chemical Communications, 2009 , # 30 p. 4566 - 4568

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Citation Number: 28

Abstract

In seeking to develop simple, waste-free methods for the synthesis of carboxylic acid derivatives, we have advanced the concept of redox esterifications and amidations. 6 These reactions, promoted by N-heterocyclic carbenes, 7 proceed via transient activated carboxylates catalytically generated by internal redox reactions of α-functionalized aldehydes including epoxyaldehydes, 8 α-haloaldehydes, 9 formylcyclopropanes, 10 and α,β-unsaturated ...