[4+2] Cycloaddition of Ketenes with N-Benzoyldiazenes Catalyzed by N-Heterocyclic Carbenes

• Published in: Angewandte Chemie (International ed.) Vol. 48; no. 1; pp. 192 - 195
• Main Authors: Huang, Xue-Liang, He, Lin, Shao, Pan-Lin, Ye, Song
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley-VCH Verlag 01.01.2009; WILEY-VCH Verlag; WILEY‐VCH Verlag; Wiley
• Subjects: Aza Compounds - chemistry; Benzene - chemistry; carbenes; Catalysis; Chemistry; Chemistry, Multidisciplinary; Cyclization; cycloaddition; enantioselectivity; Heterocyclic Compounds - chemistry; ketenes; Ketones - chemical synthesis; Ketones - chemistry; Methane - analogs & derivatives; Methane - chemistry; Molecular Structure; Physical Sciences; Science & Technology; Stereoisomerism; synthetic methods; enantioselectivity; HIGHLY ENANTIOSELECTIVE SYNTHESIS; cycloaddition; ASYMMETRIC-SYNTHESIS; AZA-BETA-LACTAMS; ketenes; carbenes; BAYLIS-HILLMAN REACTION; ORGANOCATALYSIS; ENONES; synthetic methods
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.200804487

Enantioselectivity switch: A catalytic enantioselective [4+2] cycloaddition reaction of alkylarylketenes with N‐aryl‐N′‐benzoyldiazenes or N,N′‐dibenzoyldiazenes to give 1,3,4‐oxadiazin‐6‐ones 1 was developed by employing N‐heterocyclic carbene (NHC) catalysts. The enantioselectivities could be switched for most reactions by changing the substituents on the NHC catalyst. TBS=tert‐butyldimethylsilyl, Mes=2,4,6‐trimethylphenyl.