Highly Enantioselective Intermolecular Stetter Reaction of Simple Acrylates: Synthesis of a-Chiral ?-Ketoesters

• Published in: Chemistry : a European journal Vol. 18; no. 51; pp. 16297 - 16301
• Main Authors: Wurz, Nathalie E., Daniliuc, Constantin G., Glorius, Frank
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 14.12.2012; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; CATALYSIS; N-HETEROCYCLIC CARBENE; ACID; Stetter reaction; BENZOIN CONDENSATION; acrylates; ALDEHYDES; asymmetric catalysis; CYCLOPROPENES; ENALS; organocatalysis; TRIAZOLIUM SALTS; synthetic methods; HYDROACYLATION; N-heterocyclic carbenes

Simple Stetter: A novel N-heterocyclic carbene (NHC) was designed by combining an electron-rich 2,6-dimethoxy substituent and an underestimated yet promising chiral motif. With this NHC in hand, a highly enantioselective intermolecular Stetter reaction of simple acrylates was developed, yielding ver...