Organic letters

Highly Chemo-and Enantioselective Cross-Benzoin Reaction of Aliphatic Aldehydes and α-Ketoesters

K Thai, SM Langdon, F Bilodeau, M Gravel

Index: Thai, Karen; Langdon, Steven M.; Bilodeau, Francois; Gravel, Michel Organic Letters, 2013 , vol. 15, # 9 p. 2214 - 2217

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Citation Number: 31

Abstract

An electron-deficient, valine-derived triazolium salt is shown to catalyze a highly chemo-and enantioselective cross-benzoin reaction between aliphatic aldehydes and α-ketoesters. This methodology represents the first high yielding and highly enantioselective intermolecular cross-benzoin reaction using an organocatalyst (up to 94% ee). Further diastereoselective reduction of the products gives access to densely oxygenated compounds with high ...