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Synthesis, chiral separation, and absolute configuration of bis‐( N ‐aryl) atropisomeric triads: 1,2‐Bis‐[4‐methyl‐2‐(thi)oxo‐2,3‐dihydrothiazol‐3‐yl]‐benzene
Author(s) -
Roussel Christian,
KaidSlimane Radia,
Andreoli Federico,
Renaudin Mailis,
Vanthuyne Nicolas
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20599
Subject(s) - chemistry , enantiomer , absolute configuration , benzene , chirality (physics) , chiral column chromatography , chiral derivatizing agent , aryl , atropisomer , stereochemistry , organic chemistry , chiral symmetry , physics , alkyl , quantum mechanics , nambu–jona lasinio model , quark
In this work, a series of 1,2‐bis‐[4‐methyl‐2‐(thi)oxo‐2,3‐dihydrothiazol‐3‐yl]‐benzene has been prepared. These atropisomeric molecular triads were exclusively found to exist in the anti ‐form. They were separated into enantiomers by liquid chromatography on a chiral support. The absolute configurations of the enantiomers were determined using a chemical correlation method together with chiral chromatography. The barriers to interconversion of the enantiomers were determined. Chirality, 2009. © 2008 Wiley‐Liss, Inc.