Chirality sensing of amines, diamines, amino acids, amino alcohols, and α-hydroxy acids with a single probe

J Am Chem Soc. 2013 Dec 4;135(48):18052-5. doi: 10.1021/ja410428b. Epub 2013 Nov 21.

Abstract

A stereodynamic probe for determination of the absolute configuration and enantiomeric composition of chiral amines, diamines, amino alcohols, amino acids, and α-hydroxy carboxylic acids is described. The chirality sensing is based on spontaneous asymmetric transformation of the first kind with stereolabile binaphtholate boron and zinc complexes. The substrate binding and chiral amplification processes yield a distinctive chiroptical sensor output at high wavelength that can be used for rapid and accurate ee detection of minute sample amounts.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amines / chemistry*
  • Amino Acids / chemistry*
  • Amino Alcohols / chemistry*
  • Boron / chemistry
  • Coordination Complexes / chemistry
  • Diamines / chemistry*
  • Hydroxy Acids / chemistry*
  • Models, Molecular
  • Stereoisomerism
  • Zinc / chemistry

Substances

  • Amines
  • Amino Acids
  • Amino Alcohols
  • Coordination Complexes
  • Diamines
  • Hydroxy Acids
  • Zinc
  • Boron