Diastereo- and enantioselective synthesis of alpha,gamma-diaminobutyric acid derivatives via Cu-catalyzed asymmetric Michael reaction

Org Lett. 2010 Mar 5;12(5):1080-3. doi: 10.1021/ol100060t.

Abstract

The first highly diastereo- and enantioselective catalytic asymmetric Michael addition of glycine derivatives to nitroalkenes have been developed. The enantioselectivity of ortho-substituted products can be significantly improved by using a new 1,2-P,N-ferrocene ligand L5. The alpha,gamma-diaminoacid derivative was obtained without the loss of optical activity from the adduct.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminobutyrates / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Ferrous Compounds / chemistry
  • Ligands
  • Metallocenes
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Aminobutyrates
  • Ferrous Compounds
  • Ligands
  • Metallocenes
  • 2,4-diaminobutyric acid
  • Copper
  • ferrocene