4.5 Article

Metal-Free Asymmetric 1,3-Dipolar Cycloaddition of N-Arylmaleimides to Azomethine Ylides Catalyzed by Chiral Tertiary Amine Thiourea

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 23, Pages 4472-4478

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100205

Keywords

Cycloaddition; Organocatalysis; Diastereoselectivity; Enantioselectivity; Azomethine ylides

Funding

  1. National Natural Science Foundation of China (NSFC) [20802075, 21042006]
  2. Chinese Academy of Sciences

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The first metal-free asymmetric 1,3-dipolar cycloaddition of N-arylmaleimides to azomethine ylides catalyzed by chiral tertiary amine thiourea to form multiply substituted pyrrolidines in excellent yields (up to 89%) and enantioselectivities (up to 96% ee) is presented. This procedure allows a rapid diversity-oriented synthesis of chiral pyrrolidine derivatives with high optical purity.

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