The enantioselective synthesis of alpha-amino acid derivatives via organoboranes

J Am Chem Soc. 2002 Aug 14;124(32):9348-9. doi: 10.1021/ja017522e.

Abstract

Optically active (S)-alpha-amino acids are prepared in 54-95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine, and base. The enantiomeric (R)-alpha-amino acids are available in 59-92% ee (3 cases) by using cinchonine as the chiral control element.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Boranes / chemistry*
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Boranes
  • Organometallic Compounds