4.8 Article

Phosphine-Catalyzed Asymmetric Umpolung Addition of Trifluoromethyl Ketimines to Morita-Baylis-Hillman Carbonates

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 42, Pages 13316-13320

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201607918

Keywords

asymmetric catalysis; enantioselectivity; fluorine; organocatalysis; umpolung

Funding

  1. 973 Programs [2015CB856600]
  2. National Natural Science Foundation of China [21372084, 21425205]
  3. Changjiang Scholars and Innovative Research Team in University (PCSIRT)

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A novel phosphine-catalyzed, highly enantioselective umpolung addition of trifluoromethyl ketimines to Morita-Baylis-Hillman carbonates was developed and it provides facile access to optically active trifluoromethyl amines with a chiral tertiary stereocenter under mild reaction conditions. The salient features of this reaction include general substrate scope, mild reaction conditions, good yields, high enantioselectivity, ease of scale-up to gram scale, and further transformations of the products.

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