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

Authors

  • Pan-Lin Shao,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-6255-4449
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  • Xiang-Yu Chen,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-6255-4449
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  • Prof. Dr. Song Ye

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-6255-4449
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  • Financial support from the National Natural Science Foundation of China (nos. 20872143, 20932008), the Ministry of Science and Technology of China (no. 2009ZX-5909501-018), and the Chinese Academy of Sciences is gratefully acknowledged.

Abstract

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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-toluenesulfonyl).

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