Fluorinative hydrolysis of phosphorothioic acid esters with a binaphthyl group through axis-to-center chirality transfer leading to the formation of P-chiral phosphorothioic monofluoridic acid salts

Chem Commun (Camb). 2014 Oct 25;50(83):12473-5. doi: 10.1039/c4cc05198j.

Abstract

Asymmetric synthesis of P-chiral phosphorothioic monofluoridic acid ammonium salts was achieved via axis-to-center chirality transfer reactions by using phosphorothioic acid O-esters with a binaphthyl group, and the absolute stereochemistry of the salts was determined by X-ray analyses and by comparison of their CD spectra.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ammonium Compounds / chemical synthesis
  • Ammonium Compounds / chemistry*
  • Crystallography, X-Ray
  • Fluorides / chemical synthesis
  • Fluorides / chemistry*
  • Halogenation
  • Hydrolysis
  • Models, Molecular
  • Naphthalenes / chemistry
  • Phosphoric Acids / chemical synthesis
  • Phosphoric Acids / chemistry*
  • Salts / chemistry*
  • Stereoisomerism

Substances

  • Ammonium Compounds
  • Naphthalenes
  • Phosphoric Acids
  • Salts
  • Fluorides