Catalytic diastereoselective synthesis of diquinanes from acyclic precursors

J Am Chem Soc. 2003 Apr 2;125(13):3682-3. doi: 10.1021/ja030022w.

Abstract

Upon exposure of up to 10 mol % tributylphosphine, electron-deficient 1,7-enynes undergo [3 + 2] cycloaddition to afford bicyclo[3:3:0] ring systems. In all but one case, products were obtained in >95:5 de, as determined by 1H NMR. This methodology enables concise and diastereoselective access to diquinane ring systems, whereby three contiguous stereogenic centers are set in a single manipulation.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Catalysis
  • Cyclization
  • Cyclopentanes / chemical synthesis*
  • Ketones / chemistry*
  • Phosphines / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Alkynes
  • Bridged Bicyclo Compounds
  • Cyclopentanes
  • Ketones
  • Phosphines