4.8 Article

Chiral Calcium VAPOL Phosphate Mediated Asymmetric Chlorination and Michael Reactions of 3-Substituted Oxindoles

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 10, Pages 3339-3341

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja109824x

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Funding

  1. National Institutes of Health (NIH) [GM-082935]
  2. National Science Foundation [NSF-0847108]
  3. Division Of Chemistry
  4. Direct For Mathematical & Physical Scien [0847108] Funding Source: National Science Foundation

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We disclose a novel high yielding and highly enantioselective chiral calcium VAPOL phosphate-catalyzed chlorination of 3-substituted oxindoles with N-chlorosuccinimide (NCS). The reaction conditions are also shown to be effective for the catalytic enantioselective Michael addition of 3-aryloxindoles to methyl vinyl ketone.

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