Enantioselective addition of boronates to acyl imines catalyzed by chiral biphenols.
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.
Bishop
Joshua A
JA
Department of Chemistry, Center for Chemical Methodology and Library Development at Boston University (CMLD-BU), Life Science and Engineering Building, Boston University, 24 Cummington Street, Boston, MA 02215, USA.
Lou
Sha
S
Schaus
Scott E
SE
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
D001897:Boronic Acids; D007097:Imines; D010636:Phenols