The Bull–James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction12. Issue 46 (6th September 2016)

• Record Type: Journal Article
• Authors: Brittain, William D. G.; Chapin, Brette M.; Zhai, Wenlei; Lynch, Vincent M.; Buckley, Benjamin R.; Anslyn, Eric V.; Fossey, John S.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 46(2016)
• Page Start: 10778
• Page End: 10782
• Publication Date: 2016-09-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01623e
• Languages: English
• ISSNs: 1477-0520

Abstract

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 1 H NMR spectroscopy. 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 1 H 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.