Synthesis of rare earth catalysts and their applications for enantioselective synthesis of heterocyclic β-amino alcohols

J Org Chem. 2011 Dec 2;76(23):9801-8. doi: 10.1021/jo2019015. Epub 2011 Nov 8.

Abstract

A new family of chiral lanthanide complexes derived from (R)-binaphthol has been synthesized by a one-pot procedure using only commercially available substrates. These complexes were evaluated for the aminolysis of meso-epoxides and proved to be efficient enantioselective catalysts. The samarium complex coordinated by two (R)-binaphthoxide ligands was the most enantioselective catalyst of this series. β-Amino alcohols including heterocycles have been isolated with enantiomeric excesses up to 84%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry
  • Catalysis
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Metals, Rare Earth / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*

Substances

  • Amino Alcohols
  • Heterocyclic Compounds
  • Metals, Rare Earth
  • Organometallic Compounds