C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine--an intermediate for APN inhibitor

J Org Chem. 2012 May 4;77(9):4375-84. doi: 10.1021/jo300349f. Epub 2012 Apr 22.

Abstract

Recyclable chiral amide-based organocatalyst 5 efficiently catalyzed asymmetric Strecker reaction of various aromatic and aliphatic N-benzhydrylimines with ethyl cyanoformate as cyanide source at -10 °C to give a high yield (95%) of α-aminonitriles with excellent chiral induction (ee, up to 99%) with the added advantage of recyclability. Based on experimental observations a probable mechanism was proposed for this reaction. This protocol with catalyst 5 was extended for the synthesis of (R)-phenylalanine and pharmaceutically important drug intermediate (R)-3-phenylpropane-1,2-diamine in high yield with high enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • CD13 Antigens / antagonists & inhibitors*
  • CD13 Antigens / chemistry*
  • Catalysis
  • Diamines / chemical synthesis
  • Diamines / chemistry*
  • Diamines / pharmacology
  • Molecular Structure
  • Nitriles / chemistry*
  • Stereoisomerism

Substances

  • (R)-3-phenylpropane-1,2-diame
  • Amino Acids
  • Diamines
  • Nitriles
  • CD13 Antigens