Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement

Org Biomol Chem. 2013 May 21;11(19):3128-44. doi: 10.1039/c3ob40115d. Epub 2013 Mar 28.

Abstract

Intramolecular conjugate displacement (ICD), the process illustrated in , has been applied to the Morita-Baylis-Hillman adducts formed from (5S)-5-(l-menthyloxy)-2(5H)-furanone and aldehydes that are substituted in the γ- or δ-position by geminal phenylthio groups. When the initial Morita-Baylis-Hillman alcohols are acetylated and oxidized to geminal sulfones, deprotonation causes ring closure by ICD (2.5→2.6). Hydrogenation, DIBAL-H reduction and desulfonylation releases an optically pure carbocycle.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis
  • Alcohols / chemistry*
  • Cyclization
  • Hydrocarbons, Cyclic / chemical synthesis*
  • Hydrocarbons, Cyclic / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Sulfones / chemical synthesis
  • Sulfones / chemistry*

Substances

  • Alcohols
  • Hydrocarbons, Cyclic
  • Sulfones