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“Hexacarboxytrindanes”: Benzene Rings with Homotopic Faces as Scaffolds for the Construction of D 3 Chiral Architectures
Author(s) -
Borsato Giuseppe,
Crisma Marco,
De Lucchi Ottorino,
Lucchini Vittorio,
Zambon Alfonso
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502262
Subject(s) - epimer , benzene , resolution (logic) , molecule , asymmetry , transesterification , macromolecule , chemistry , symmetry (geometry) , lithium (medication) , stereochemistry , crystallography , materials science , physics , mathematics , organic chemistry , computer science , quantum mechanics , geometry , catalysis , artificial intelligence , medicine , biochemistry , endocrinology
Thermodynamically driven epimerization at the trindane benzylic positions of “hexacarboxytrindanes” generates benzene rings with D 3 symmetry and with R or S homotopic faces. Almost total resolution towards S trindanes was achieved by epimerization and transesterification with lithium (−)‐mentholate. These structures are attractive cores for the construction of macromolecules in which asymmetry is induced by the center of the molecule.