The Bull-James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction.
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 by1H 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.
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands B15 2TT, UK. j.s.fossey@bham.ac.uk and Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA. anslyn@austin.utexas.edu.
William D G
http://orcid.org/0000-0002-2876-5895
WD
Brittain
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands B15 2TT, UK. j.s.fossey@bham.ac.uk and Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA. anslyn@austin.utexas.edu.
Brette M
BM
Chapin
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands B15 2TT, UK. j.s.fossey@bham.ac.uk and Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA. anslyn@austin.utexas.edu.
Wenlei
W
Zhai
Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA. anslyn@austin.utexas.edu.
Vincent M
VM
Lynch
Department of Chemistry, Loughborough University, Loughborough, Leicestershire, LE11 3TU, UK.
Benjamin R
BR
Buckley
Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA. anslyn@austin.utexas.edu.
Eric V
EV
Anslyn
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands B15 2TT, UK. j.s.fossey@bham.ac.uk.
John S
http://orcid.org/0000-0002-2626-5117
JS
Fossey