Optical resolution of aromatic alcohols using silica nanoparticles grafted with helicene

Org Lett. 2012 Jun 15;14(12):3123-5. doi: 10.1021/ol301206r. Epub 2012 May 23.

Abstract

Optically active silica nanoparticles, with a 70-nm diameter, grafted with (P)-1,12-dimethyl-8-methoxycarbonylbenzo[c]phenanthrene-5-carboxyamide were synthesized, and their use in the kinetic resolution of aromatic alcohols was examined. Up to 61% ee for (S)-2,2-dimethyl-1-phenyl-1-propanol was obtained by a preferential precipitation of aggregates formed with (P)-nanoparticles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Molecular Structure
  • Nanoparticles / chemistry*
  • Polycyclic Compounds / chemistry*
  • Silicon Dioxide / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Polycyclic Compounds
  • helicenes
  • Silicon Dioxide