Highly enantioselective phase-transfer catalytic alkylation in the preparation of non-natural alpha-amino acids via solid phase synthesis using aldimine linker

J Org Chem. 2005 Mar 4;70(5):1904-6. doi: 10.1021/jo0481957.

Abstract

A new Merrifield-resin-derived glycinimine tert-butyl ester (9) was prepared and applied to the enantioselective synthesis of non-natural alpha-amino acids. High enantioselectivities (86 to >99% ee) were accomplished by employing the aldimine linker under phase-transfer alkylation conditions, using 50% aqueous CsOH in toluene/chloroform (7:3) at 0 degrees C in the presence of N-(9-anthracenylmethyl)-O(9)-allylcinchonidium bromide (10 mol %).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amino Acids / chemical synthesis*
  • Catalysis
  • Cross-Linking Reagents / chemistry*
  • Imines / chemistry*
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Amino Acids
  • Cross-Linking Reagents
  • Imines