The first example of enantioselective allyl transfer from a linear homoallylic alcohol to an aldehyde

Org Lett. 2002 Aug 22;4(17):2985-7. doi: 10.1021/ol0263999.

Abstract

[reaction: see text] The first example of enantioselective linear homoallylic alcohol transfer reaction was revealed. In all cases, the whole rearrangement is thermodynamically favorable and a steric effect is the driving force of this reaction. The preservation of the stereocenter and olefin geometry together with the isolation of gamma-adduct homoallylic alcohols in one isomeric form have warranted the proposed mechanism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Aldehydes / chemistry
  • Allyl Compounds / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Macrolides
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Allyl Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Macrolides
  • amphidinolide K