Enantioselective catalytic addition of HCN to ketoimines. Catalytic synthesis of quaternary amino acids

Org Lett. 2000 Mar 23;2(6):867-70. doi: 10.1021/ol005636+.

Abstract

[formula: see text] Highly enantioselective addition of HCN to ketoimines has been achieved for the first time using readily accessible and recyclable Schiff base catalysts. Essentially quantitative isolated yield and enantioselectivity of up to 95% ee was obtained. Furthermore, some of the Strecker adducts could be recrystallized in high recovery, yielding optically pure materials. Conversion of the alpha-aminonitrile adducts to the corresponding alpha-quaternary alpha-amino acids was effected in high yield by a formylation/hydrolysis sequence.

Publication types

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

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Hydrogen Cyanide*
  • Imines / chemistry*
  • Indicators and Reagents
  • Schiff Bases
  • Stereoisomerism

Substances

  • Amino Acids
  • Imines
  • Indicators and Reagents
  • Schiff Bases
  • Hydrogen Cyanide