Asymmetric synthesis of α-amino acids by reduction of N-tert-butanesulfinyl ketimine esters

J Org Chem. 2011 May 6;76(9):3409-15. doi: 10.1021/jo200401a. Epub 2011 Apr 11.

Abstract

A highly regio- and diastereoselective reduction of various N-tert-butanesulfinyl ketimine esters with L-Selectride resulting in the formation of α-amino acids is reported. This method is quite general and also practical for the preparation of both enantiomers of aryl or aliphatic α-amino acids in high yields.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Esters
  • Imines / chemistry*
  • Nitriles / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Amino Acids
  • Esters
  • Imines
  • Nitriles
  • ketimine