4.7 Article

Organocatalytic Asymmetric Addition of Thiols to Trifluoromethylaldimine: An Efficient Approach to Chiral Trifluoromethylated N,S-Acetals

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 2-3, Pages 327-331

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200845

Keywords

asymmetric catalysis; bifunctional organocatalysts; enantioselectivity; N,S-acetals; trifluoromethyl group

Funding

  1. 973 Program [2011CB808600]
  2. National Natural Science Foundation of China [20972117, 21172176]
  3. Fundamental Research Funds for the Central Universities
  4. Large-scale Instrument And Equipment Sharing Foundation of Wuhan University
  5. [NCET-10-0649]
  6. [IRT1030]

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The first organocatalytic asymmetric addition of thiols to trifluoromethylaldimine for the construction of chiral trifluoromethylated N,S-acetals has been achieved in high yields (up to 99%) and excellent enantioselectivities (up to 95% ee) with 1mol% of a bifunctional organocatalyst.

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