Practical and efficient enantioselective synthesis of alpha-amino acids in aqueous media

Org Biomol Chem. 2004 Dec 21;2(24):3584-7. doi: 10.1039/b413017k. Epub 2004 Nov 9.

Abstract

Enantiomerically pure natural and unnatural alpha-amino acids have been synthesized from a chiral methyleneoxazolidinone by means of a highly diastereoselective 1,4-conjugate addition of alkyl iodides in aqueous media. The zinc-copper conjugate addition reaction exhibits high chemoselectivity, with the possibility of using functionalized iodides, to afford a single diastereomer in short reaction times and with good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Molecular Conformation
  • Stereoisomerism
  • Water / chemistry*

Substances

  • Amino Acids
  • Water