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Atropisomerism, Biphenyls, and Fluorine: A Comparison of Rotational Barriers and Twist Angles
Author(s) -
Leroux Frédéric
Publication year - 2004
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200300906
Subject(s) - atropisomer , biphenyl , chemistry , axial chirality , twist , fluorine , combinatorial chemistry , unit (ring theory) , reagent , stereochemistry , computational chemistry , organic chemistry , enantioselective synthesis , catalysis , mathematics , geometry , mathematics education
Doing the twist : Atropisomerism of axially chiral biaryls is of increasing importance because the biaryl unit can be found in numerous biologically active natural products. Furthermore, biaryls are the most efficient reagents and ligands in asymmetric synthesis and the biphenyl unit belongs to the six or seven “privileged structures” in pharmaceutical research. Attention has to be paid to the factors which influence the electronic and geometric properties of the biaryl unit. Fluorine seems to be the ideal molecular tool for fine‐tuning these properties.