Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay

J Am Chem Soc. 2018 Mar 14;140(10):3514-3517. doi: 10.1021/jacs.7b13710. Epub 2018 Feb 27.

Abstract

We report a stereoselective formal [3 + 2] cycloaddition of cyclopropyl ketones and radical-acceptor alkenes to form polysubstituted cyclopentane derivatives. Catalyzed by a chiral Ti(salen) complex, the cycloaddition occurs via a radical redox-relay mechanism and constructs two C-C bonds and two contiguous stereogenic centers with generally excellent diastereo- and enantioselectivity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cycloaddition Reaction*
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry
  • Free Radicals / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism
  • Titanium / chemistry*

Substances

  • Alkenes
  • Cyclopentanes
  • Free Radicals
  • Ketones
  • Titanium