4.7 Article

Organocatalytic One-Pot Asymmetric Synthesis of Thiolated Spiro-γ-lactam Oxindoles Bearing Three Stereocenters

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 13, 页码 5362-5369

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00653

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资金

  1. Joseph P. Healey Research Grant
  2. Center for Green Chemistry at the University of Massachusetts Boston
  3. NSF-MRI program [CHE-1039027]

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The first asymmetric synthesis of spiro-gamma-lactam oxindoles bearing three stereocenters is reported. One-pot thiol-Michael/Mannich/lactamization reactions promoted by a recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst afford products in moderate to good yields with up to 95% ee and 6:1 dr.

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