4.6 Article

A highly enantioselective Friedel-Crafts reaction of 3,5-dimethoxylphenol with nitroolefins mediated by a bifunctional quinine derived thiourea catalyst

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 16, Pages 3401-3407

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00372b

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Funding

  1. National Natural Science Foundation of China [21402177]
  2. Natural Science Foundation of Zhejiang Province [LY17B020003]
  3. Zhejiang University of Science Technology

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A useful enantioselective Friedel-Crafts reaction of 3,5-dimethoxylphenol with nitroolefins catalyzed by a bifunctional quinine derived thiourea catalyst 9 was developed. The Michael addition products could be obtained in good to high yields (68-92%) and with excellent enantioselectivities (89-98% ee). Such a reaction is exceptionally attractive in virtue of its simple protocol, ready availability of the starting materials, and practical applications of the products.

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