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Enantioselective addition of boronates to acyl imines catalyzed by chiral biphenols.

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.

SUBMITTER: Bishop JA 

PROVIDER: S-EPMC2819183 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature

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Enantioselective addition of boronates to acyl imines catalyzed by chiral biphenols.

Bishop Joshua A JA   Lou Sha S   Schaus Scott E SE  

Angewandte Chemie (International ed. in English) 20090101 24

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. ...[more]

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