Highly enantioselective γ-amination of α,β-unsaturated acyl chlorides with azodicarboxylates: efficient synthesis of chiral γ-amino acid derivatives

J Am Chem Soc. 2011 Oct 12;133(40):15894-7. doi: 10.1021/ja206819y. Epub 2011 Sep 15.

Abstract

The cinchona alkaloid-catalyzed γ-amination of α,β-unsaturated acyl chlorides with azodicarboxylates to give the corresponding dihydropyridazinones in good yields with high enantioselectivities has been developed. Reductive ring opening of the dihydropyridazinones afforded series of cyclic and acyclic γ-amino acid derivatives in good yields with high enantiopurity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Chlorides / chemistry*
  • Cinchona Alkaloids / chemistry*
  • Pyridazines / chemical synthesis
  • Pyridazines / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Carboxylic Acids
  • Chlorides
  • Cinchona Alkaloids
  • Pyridazines