“Hexacarboxytrindanes”: Benzene Rings with Homotopic Faces as Scaffolds for the Construction of  D  3  Chiral Architectures | Zendy

Borsato Giuseppe | Zendy; Crisma Marco | Zendy; De Lucchi Ottorino | Zendy; Lucchini Vittorio | Zendy; Zambon Alfonso | Zendy

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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.

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