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Front Cover: Inversion of the Axial Information during Oxidative Aromatization in the Synthesis of Axially Chiral Biaryls with Organocatalysis as a Key Step (Chem. Eur. J. 20/2020)
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 - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000776
Subject(s) - aromatization , enantioselective synthesis , axial chirality , chemistry , axial symmetry , inversion (geology) , chirality (physics) , stereochemistry , catalysis , computational chemistry , combinatorial chemistry , organic chemistry , physics , mathematics , chiral anomaly , geometry , particle physics , fermion , nambu–jona lasinio model , biology , paleontology , structural basin
A new pot‐economical and highly enantioselective synthesis of axially chiral biaryls was developed. The protocol features a domino reaction mediated by an organocatalyst, and a subsequent aromatization preceded by Nef reaction. The axial information of the precursor, which existed as a single axial conformer, was temporarily lost in the intermediate step, and it reemerges with a complete inversion in the final biaryls. The resulting absolute configuration on the chiral axis of the biaryl products was fixed at the aromatization step by a phenomenon of central to axial chirality transfer. More information can be found in the Full Paper by Y. Hayashi et al. on page 4524.