Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure alpha,beta-amino alcohol groups

Org Lett. 2004 Apr 15;6(8):1189-92. doi: 10.1021/ol036122o.

Abstract

Calixarenes bearing optically pure alpha,beta-amino alcohol groups at their lower rim exhibit exceptional and efficient chiral recognition ability in discrimination of racemic mandelic acid, 2,3-dibenzoyltartaric acid and 2-hydroxy-3-methylbutyric acid. [structure: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / chemistry*
  • Calixarenes / chemistry*
  • Carboxylic Acids / chemistry*
  • Hemiterpenes
  • Mandelic Acids / chemistry
  • Molecular Structure
  • Pentanoic Acids / chemistry
  • Phenols / chemistry*
  • Stereoisomerism
  • Tartrates / chemistry

Substances

  • Amino Alcohols
  • Carboxylic Acids
  • Hemiterpenes
  • Mandelic Acids
  • Pentanoic Acids
  • Phenols
  • Tartrates
  • calix(4)arene
  • Calixarenes
  • isovaleric acid
  • 2,3-bis(benzoyloxy)tartaric acid
  • mandelic acid