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.
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.
Joshua A
JA
Bishop
Sha
S
Lou
Scott E
SE
Schaus
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