Enantioselective synthetic method for alpha-alkylserine via phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4- carbonylcamphorsultam

J Org Chem. 2005 May 13;70(10):4158-61. doi: 10.1021/jo050197j.

Abstract

[reaction: see text] An enantioselective synthetic method for alpha-alkylserines by the phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4-carbonylcamphorsultam (4a) was developed. The phase-transfer catalytic alpha-alkylation of 4a using P2-Et at -78 degrees C gave alpha-alkylation (75 to approximately 99%, 90 to approximately 97% de), which could be easily hydrolyzed to alpha-alkylserines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Carboxylic Acids / chemistry
  • Esters / chemistry
  • Eugenol / analogs & derivatives*
  • Eugenol / chemistry*
  • Models, Chemical
  • Oxazoles / chemistry*
  • Serine / analogs & derivatives*
  • Serine / chemical synthesis
  • Serine / chemistry
  • Stereoisomerism

Substances

  • 2-phenyl-2-oxazoline-4- carbonylcamphorsultam
  • 2-phenyl-2-oxazoline-4-carboxylic acid tert-butyl ester
  • Carboxylic Acids
  • Esters
  • Oxazoles
  • Eugenol
  • Serine