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Synfacts 2010(12): 1424-1424  
DOI: 10.1055/s-0030-1258926
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Formal [3+2] Cycloaddition of Ketenes and Oxaziridines

Contributor(s): Benjamin List, Ilija Čorić
P.-L. Shao, X.-Y. Chen, S. Ye*
Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. of China
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

The catalytic asymmetric formal [3+2] cycloaddition of ketenes and oxaziridines has been reported. The N-heterocyclic carbene derived from 1 and the cinchona alkaloid derivative 2 were found to be efficient catalysts for the reaction of di- and monosubstituted ketenes with oxaziridine 4, respectively. Oxazolidin-4-ones 5 and 7 were obtained in moderate yields and with high enantioselectivity.