4.8 Article

(Dynamic) Kinetic Resolution of Enamines/Imines: Enantioselective N-Heterocyclic Carbene Catalyzed [3+3] Annulation of Bromoenals and Enamines/Imines

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 4, Pages 1183-1187

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813047

Keywords

annulations; heterocycles; kinetic resolution; N-heterocyclic carbene; organocatalysis

Funding

  1. National Natural Science Foundation of China [21425207, 21521002, 21831008]
  2. Chinese Academy of Sciences

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The enantioselective N-heterocyclic carbene catalyzed [3+3] annulation of alpha-bromoenals by dynamic kinetic resolution (DKR) of enamines and normal resolution of alpha,alpha-disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo- and enantioselectivities, and a high selective factor (up to 83) was realized for the resolution of alpha,alpha-disubstituted imines.

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