Enantioseparation of 1-arylethanols via a supramolecular chiral host consisting of N-(2-naphthoyl)-L-aspartic acid and an achiral diamine

Org Biomol Chem. 2012 Mar 7;10(9):1877-82. doi: 10.1039/c2ob06475h. Epub 2012 Jan 25.

Abstract

A supramolecular chiral host consisting of N-(2-naphthoyl)-L-aspartic acid (L-1) and meso-1,2-diphenylethylenediamine (2) is effective in enantioseparation of 1-arylethanols (up to 96% ee with 100% inclusion ratio). Here we report three different methods to prepare the inclusion crystals and discuss the chiral recognition mechanism on the basis of X-ray crystallography results.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspartic Acid / analogs & derivatives*
  • Aspartic Acid / chemistry
  • Crystallography, X-Ray
  • Diamines / chemistry*
  • Ethanol / chemistry*
  • Ethanol / isolation & purification
  • Models, Molecular
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Stereoisomerism

Substances

  • Diamines
  • Naphthalenes
  • Aspartic Acid
  • Ethanol