4.7 Article

Stereoselective Mannich Reaction of S-Phenyl Thioesters Catalyzed by Bifunctional Organocatalysts

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 2-3, Pages 523-529

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400735

Keywords

enantioselective; imine; mannich reaction; organocatalysis; thioester

Funding

  1. Welch Foundation [AX-1573]
  2. National Institute on Minority Health and Health Disparities from the National Institutes of Health [G12 MD007591]

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A highly stereoselective Mannich reaction of S-phenyl thioesters was achieved by using bifunctional thiourea catalysts. Using a quinine-derived C6'-urea catalyst, the direct Mannich products of N-tosyl imines and S-phenyl thioesters were obtained in high yields and excellent diastereo- and enantioselectivities.

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