Efficient synthesis of alpha-aryl-/heteroaryl-substituted beta-amino acids via Ni(II) complex through the Suzuki coupling reaction

J Org Chem. 2009 Aug 7;74(15):5656-9. doi: 10.1021/jo900469d.

Abstract

We described a synthesis method by first using chlorotrimethylsilane as the activator to brominate the Ni(II) complex of the beta-alanine Schiff's base [beta-AlaNi(II)PABA] 1 and developed it to prepare beta-amino acids 5. The procedure involves a Suzuki coupling reaction between boric acids and the bromoenone 2, followed by hydrogenation and hydrolysis. This is the first report of the application of the Ni (II) complex [beta-AlaNi(II)PABA], which represents an attractive route to afford alpha-aryl-/heteroaryl-substituted beta-amino acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Nickel / chemistry*
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • Trimethylsilyl Compounds / chemistry

Substances

  • Amino Acids
  • Organometallic Compounds
  • Trimethylsilyl Compounds
  • trimethylchlorosilane
  • Nickel