Stereoselective synthesis of syn and anti 1,2-hydroxyalkyl moieties by Cu-catalyzed asymmetric allylic alkylation

Chem Commun (Camb). 2011 May 28;47(20):5843-5. doi: 10.1039/c0cc05161f. Epub 2011 Apr 18.

Abstract

A stereoselective synthesis of 1,2-hydroxyalkyl moieties is described herein. These valuable building blocks are obtained with complete regiocontrol and excellent stereocontrol both for the syn or the anti products, by choosing the appropriate enantiomer of the ligand in a copper-catalyzed asymmetric allylic alkylation of δ-alkoxy-substituted allyl bromides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Allyl Compounds / chemistry
  • Catalysis
  • Copper / chemistry*
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Copper
  • allyl bromide