4.5 Article

Enantioselective Synthesis of Isatin-Derived α-(Trifluoromethyl)imine Derivatives: Phosphine-Catalyzed γ-Addition of α-(Trifluoromethyl)imines and Allenoates

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 11, Pages 1552-1560

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700048

Keywords

alpha-(Trifluoromethyl)imines; gamma-Addition reactions; Asymmetric catalysis; Phosphanes; Chirality

Funding

  1. National Basic Research Program of China [(973)-2015CB856603]
  2. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  3. National Natural Science Foundation of China [20472096, 21372241, 21572052, 20672127, 21421091, 21372250, 21121062, 21302203, 20732008]
  4. Fundamental Research Funds for the Central Universities

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We have described the first asymmetric umpolung gamma-addition reaction of isatin-derived alpha-(trifluoromethyl)imines and allenoates. A chiral multifunctional phosphine catalyst derived from an amino acid promotes this reaction very well un-der mild conditions to give a series of enantiomerically enriched isatin-derived alpha-(trifluoromethyl)imine derivatives in high yields and with moderate to good enantioselectivities.

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