Enantioselective Boronate Additions to <i>N</i>-Acyl Quinoliniums Catalyzed by Tartaric Acid

Abstract

Tartaric acid catalyzes the asymmetric addition of vinylboronates to N-acyl quinoliniums, affording highly enantioenriched dihydroquinolines. The catalyst serves to activate the boronate through a ligand-exchange reaction and generates the N-acyl quinolinium in situ from the stable quinoline-derived N,O-acetal.