Organic letters

Asymmetric Access to the Smallest Enolate Intermediate via Organocatalytic Activation of Acetic Ester

S Chen, L Hao, Y Zhang, B Tiwari, YR Chi

Index: Chen, Shaojin; Hao, Lin; Zhang, Yuexia; Tiwari, Bhoopendra; Chi, Yonggui Robin Organic Letters, 2013 , vol. 15, # 22 p. 5822 - 5825

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Citation Number: 4

Abstract

An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α, β- unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively.