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Inversion of the Axial Information during Oxidative Aromatization in the Synthesis of Axially Chiral Biaryls with Organocatalysis as a Key Step
Author(s) -
Koshino Seitaro,
Takikawa Akira,
Ishida Keiichi,
Taniguchi Tohru,
Monde Kenji,
Kwon Eunsang,
Umemiya Shigenobu,
Hayashi Yujiro
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905814
Subject(s) - aromatization , enantioselective synthesis , axial chirality , chirality (physics) , axial symmetry , chemistry , oxidative phosphorylation , inversion (geology) , domino , catalysis , organic chemistry , chiral perturbation theory , physics , geometry , mathematics , particle physics , geology , paleontology , pion , biochemistry , structural basin , nambu–jona lasinio model
The pot‐economical, highly enantioselective synthesis of axially chiral biaryls was developed by using one‐pot organocatalyst‐mediated domino and aromatization reactions as key steps. The axial information of the precursor, which also has central chirality, was completely inverted in the final biaryls. The inversion of the axial information occurred in the conversion of the central chirality to the axial chirality of an oxidative aromatization step.