Enantioselective Addition of Boronates to Acyl Imines Catalyzed by Chiral Biphenols

JA Bishop, S Lou, SE Schaus

Index: Bishop, Joshua A.; Lou, Sha; Schaus, Scott E. Angewandte Chemie, International Edition, 2009 , vol. 48, # 24 p. 4337 - 4340

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Citation Number: 38

Abstract

Abstract On the big screen: A chiral biphenol catalyst screening protocol was developed for the rapid identification of enantioselective nucleophilic boronate reactions with acyl imines (see scheme). The approach successfully identified a unique catalyst for the reaction of aryl, vinyl, and alkynyl boronates. Mechanistic studies demonstrate boronate ligand exchange with the catalyst is necessary for activation towards nucleophilic addition.