Enantioselective Synthesis of Cyclobutenes by Intermolecular [2+2] Cycloaddition with Non-C2 Symmetric Digold Catalysts

J Am Chem Soc. 2017 Oct 4;139(39):13628-13631. doi: 10.1021/jacs.7b07651. Epub 2017 Sep 22.

Abstract

The enantioselective intermolecular gold(I)-catalyzed [2+2] cycloaddition of terminal alkynes and alkenes has been achieved using non-C2-chiral Josiphos digold(I) complexes as catalysts, by the formation of the monocationic complex. This new approach has been applied to the enantioselective total synthesis of rumphellaone A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cycloaddition Reaction
  • Cyclobutanes / chemical synthesis*
  • Cyclobutanes / chemistry
  • Gold / chemistry*
  • Molecular Structure
  • Sesterterpenes / chemical synthesis*
  • Sesterterpenes / chemistry
  • Stereoisomerism

Substances

  • Cyclobutanes
  • Sesterterpenes
  • rumphellaone A
  • Gold