Intramolecular palladium-catalyzed allylic alkylation: enantio- and diastereoselective synthesis of [2.2.2] bicycles

Org Lett. 2002 Oct 3;4(20):3427-30. doi: 10.1021/ol0265766.

Abstract

Pd-catalyzed asymmetric allylic alkylation provides both enantio- and diastereoselectivity in formation of bicyclo [2.2.2] octan-2,3-diones and quinuclidin-2-ones, the latter potential precursors to quinine alkaloids. [reaction: see text]

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Alkylation
  • Catalysis
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Palladium / chemistry*
  • Quinine / chemical synthesis
  • Quinine / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Heterocyclic Compounds
  • Palladium
  • Quinine