Enantioselective recognition of carboxylates: a receptor derived from alpha-aminoxy acids functions as a chiral shift reagent for carboxylic acids

J Am Chem Soc. 2005 Jun 8;127(22):7996-7. doi: 10.1021/ja051072z.

Abstract

Enantioselective recognition of carboxylates has important implications in asymmetric synthesis and drug discovery. We have prepared a novel C2-symmetric receptor 1 from alpha-aminoxy acids in a high overall yield. A series of chiral recognition studies indicate that receptor 1 not only can bind to carboxylate ions tightly but also has a good ability to recognize enantiomers of a broad variety of carboxylic acids in the 1H NMR spectra. Thus, the receptor 1 can be used as a chiral shift reagent for the determination of enantiomeric purities of chiral carboxylic acids by 1H NMR directly and rapidly.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Carboxylic Acids / analysis
  • Carboxylic Acids / chemistry*
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy / methods
  • Mandelic Acids / chemistry
  • Stereoisomerism

Substances

  • Amino Acids
  • Carboxylic Acids
  • Mandelic Acids
  • mandelic acid