4.8 Article

A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 16, Pages 5206-5209

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b01462

Keywords

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Funding

  1. MEXT (Japan)
  2. JSPS
  3. Grants-in-Aid for Scientific Research [26220803, 13J00116, 15H03778] Funding Source: KAKEN

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Chiral electrophilic selenium catalysts have been applied to catalytic asymmetric transformations of alkenes over the past two decades. However, highly enantioselective reactions with a broad substrate scope have not yet been developed. We report the first successful example of this reaction employing a catalyst based on a rigid indanol scaffold, which can be easily synthesized from a commercially available indanone. The reaction efficiently converts, beta,gamma-unsaturated carboxylic acids into various enantioenriched gamma-butenolides under mild conditions.

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