4.8 Article

Enantioselective Addition of Thiols to Imines Catalyzed by Thiourea-Quaternary Ammonium Salts

Journal

ACS CATALYSIS
Volume 3, Issue 10, Pages 2218-2221

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/cs400594e

Keywords

N,S-acetal; organocatalysis; ion-pairs catalyisis; phase-transfer catalysis; bifunctional catalyst

Funding

  1. National Basic Research Program of China (973 Program) [2010CB833200]
  2. National Natural Science Foundation of China [21032006, 203900502, 20532040, 21290180]
  3. Science and Technology Commission of Shanghai Municipality [11XD1406400]

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Asymmetric phase-transfer catalysis was first applied to the synthesis of chiral N,S-acetals by using amino acid-based bifunctional thiourea-ammonium salt catalysts. The reaction could be performed on the gram scale to give up to 93% ee and 99% yield with a catalyst loading as low as 0.1 mol % within 5 min.

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