A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization

J Am Chem Soc. 2016 Apr 27;138(16):5206-9. doi: 10.1021/jacs.6b01462. Epub 2016 Apr 15.

Abstract

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 β,γ-unsaturated carboxylic acids into various enantioenriched γ-butenolides under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't