The Bull–James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction

Research output: Contribution to journalArticle

Authors

  • William D. G. Brittain
  • Brette M. Chapin
  • Wenlei Zhai
  • Vincent M. Lynch
  • Benjamin R. Buckley
  • Eric V. Anslyn

Colleges, School and Institutes

Abstract

The Bull–James boronic acid assembly is used simultaneously as a chiral auxiliary for kinetic resolution and as a chiral shift reagent for in situ enantiomeric excess (ee) determination by 1H NMR spectroscopy. Chiral terminal alkyne-containing amines, and their corresponding chiral triazoles formed via CuAAC, were probed in situ. Selectivity factors of up to s = 4 were imparted and measured, accurate to within ±3% when compared to chiral GC.

Details

Original languageEnglish
JournalOrganic and Biomolecular Chemistry
Early online date6 Sep 2016
Publication statusE-pub ahead of print - 6 Sep 2016