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Enantioselective Addition of Boronates to Acyl Imines Catalyzed by Chiral Biphenols
Author(s) -
Bishop Joshua A.,
Lou Sha,
Schaus Scott E.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901023
Subject(s) - enantioselective synthesis , nucleophile , chemistry , catalysis , nucleophilic addition , ligand (biochemistry) , combinatorial chemistry , aryl , organic chemistry , biochemistry , alkyl , receptor
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.