Asymmetric Intramolecular Crossed-Benzoin Reactions by N-Heterocyclic Carbene Catalysis

• Published in: Angewandte Chemie International Edition Vol. 45; no. 9; pp. 1463 - 1467
• Main Authors: Enders, Dieter, Niemeier, Oliver, Balensiefer, Tim
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 20.02.2006; WILEY‐VCH Verlag; Wiley
• Subjects: asymmetric synthesis; Benzoin - chemical synthesis; Benzoin - chemistry; benzoin reaction; Catalysis; Chemistry; Chemistry, Multidisciplinary; Cyclization; heterocycles; Heterocyclic Compounds - chemistry; homogeneous catalysis; Hydrocarbons - chemistry; Methane - analogs & derivatives; Methane - chemistry; Molecular Structure; N-heterocyclic carbenes; Physical Sciences; Science & Technology; Stereoisomerism; THIAZOLIUM; benzoin reaction; ALDEHYDES; QUATERNARY CARBON CENTERS; ENANTIOSELECTIVE CONSTRUCTION; SALTS; GAMMA-BUTYROLACTONES; asymmetric synthesis; homogeneous catalysis; heterocycles; STEREOCENTERS; STETTER REACTION; LACTAMS; DIRECT ANNULATIONS; N-heterocyclic carbenes
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.200503885

Getting cross: Excellent asymmetric inductions and very good yields are achieved in the generation of a quaternary stereocenter in α‐hydroxy‐substituted tetralones by using chiral N‐heterocyclic carbene catalysts in an enantioselective intramolecular crossed‐benzoin reaction. The synthesis of the corresponding α‐hydroxyindanones with good ee values is also possible by this route.