Formal [3+2] Cycloaddition of Ketenes and Oxaziridines Catalyzed by Chiral Lewis Bases: Enantioselective Synthesis of Oxazolin‐4‐ones

• Published in: Angewandte Chemie (International ed.) Vol. 49; no. 45; pp. 8412 - 8416
• Main Authors: Shao, Pan‐Lin, Chen, Xiang‐Yu, Ye, Song
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley‐VCH Verlag 02.11.2010; WILEY-VCH Verlag; WILEY‐VCH Verlag; Wiley
• Subjects: asymmetric catalysis; Chemistry; Chemistry, Multidisciplinary; cycloaddition; ketenes; oxaziridines; oxazolidin-4-ones; Physical Sciences; Science & Technology; OXIDATION; INTERMOLECULAR STETTER REACTIONS; ASYMMETRIC-SYNTHESIS; ACID; oxazolidin-4-ones; HYDROXYLATION; ALDEHYDES; asymmetric catalysis; EPOXIDATION; cycloaddition; oxaziridines; ketenes; BETA-LACTONES; CHEMISTRY; DERIVATIVES

Choose the right cat.: A highly enantioselective synthesis of oxazolin‐4‐ones by the formal [3+2] cycloaddition of ketenes and a racemic oxaziridines has been developed (see scheme; cat.=N‐heterocyclic carbenes for disubstituted ketenes or cinchona alkaloids for monosubstituted ketenes, Ts=4‐toluene...