Catalytic asymmetric Michael addition of α,β-unsaturated aldehydes to Ni(II) complexes of the Schiff base of glycine

Org Biomol Chem. 2011 Feb 7;9(3):793-801. doi: 10.1039/c0ob00221f. Epub 2010 Nov 22.

Abstract

The conjugate addition of Ni(II) complexes of glycine Schiff base to α,β-unsaturated aldehydes catalyzed by (S)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine afforded adducts in excellent yields with up to 49:1 dr and 95% ee. This method enables the construction of two adjacent chiral centers in one step, and offers an alternative route to chiral α-amino acid derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Glycine / chemistry*
  • Models, Molecular
  • Nickel / chemistry*
  • Schiff Bases / chemistry
  • Solvents / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Schiff Bases
  • Solvents
  • Nickel
  • Glycine