Enantiomeric separation of biaryl atropisomers using cyclofructan based chiral stationary phases.
Normal phase chiral HPLC methods are presented for the enantiomeric separation of 30 biaryl atropisomers including 18 new compounds recently produced via a novel synthetic approach. Three new cyclofructan based chiral stationary phases were evaluated. Separations were achieved for all but six analytes and the LARIHC™ CF6-P alone provided 15 baseline separations. Effects of polar modifiers and temperature effects also were studied. Apparent thermodynamic parameters were determined by van't Hoff plots. Preparative scale methods were developed and employed resulting in the first ever isolation of these novel atropisomers in their pure enantiomeric form. Insights into the mechanism of retention and chiral discrimination are presented.
The University of Texas at Arlington, 700 Planetarium Place, Arlington, TX 76019, USA.
Ross M
RM
Woods
The University of Texas at Arlington, 700 Planetarium Place, Arlington, TX 76019, USA.
Darshan C
DC
Patel
The University of Texas at Arlington, 700 Planetarium Place, Arlington, TX 76019, USA.
Yeeun
Y
Lim
The University of Texas at Arlington, 700 Planetarium Place, Arlington, TX 76019, USA.
Zachary S
ZS
Breitbach
Division of Chemistry, Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX 75390, USA.
Hongyin
H
Gao
Division of Chemistry, Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX 75390, USA.
Craig
C
Keene
Division of Chemistry, Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX 75390, USA.
Gongqiang
G
Li
Division of Chemistry, Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX 75390, USA.
László
L
Kürti
The University of Texas at Arlington, 700 Planetarium Place, Arlington, TX 76019, USA; AZYP LLC, 700 Planetarium Place, Arlington, TX 76019, USA. Electronic address: sec4dwa@uta.edu.
Daniel W
DW
Armstrong
D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D005630:Fructans / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D013816:Thermodynamics
D005630:Fructans; D009930:Organic Chemicals
Atropisomers; Biaryls; Chiral HPLC; Cyclofructans; Preparative HPLC