Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: enantioselective total synthesis of (-)-mesembrine

Org Lett. 2012 Dec 21;14(24):6158-61. doi: 10.1021/ol302842h. Epub 2012 Dec 4.

Abstract

A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Hydrogenation
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Iridium / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Propanols / chemical synthesis
  • Propanols / chemistry
  • Stereoisomerism

Substances

  • Indole Alkaloids
  • Ketones
  • Propanols
  • allyl alcohol
  • Iridium
  • mesembrine