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Stereoselective synthesis of atropisomeric bipyridine N,N’-dioxides by oxidative coupling

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journal contribution
posted on 14.06.2019 by Yasuaki Fukazawa, Vladimir Yu Vaganov, Sergei A. Shipilovskikh, Aleksandr E. Rubtsov, Andrei Malkov
Bipyridine N,N′-dioxide is a structural fragment found in many bioactive compounds. Furthermore, chiral analogues secured their place as powerful Lewis base catalysts. The scope of the existing methods for the synthesis of atropisomeric bipyridine N,N′-dioxides is limited. Herein, we present a practical, highly chemo- and stereoselective method for oxidative dimerization of chiral pyridine N-oxides using O2 as a terminal oxidant. A series of 13 axially chiral bipyridine N,N′-dioxides were synthesized in up to 75% yield.

Funding

The authors thank the Russian Science Foundation for Grant No. 18-73-10156. Y.F. and A.V.M. thank the Leverhulme Trust for the research grant (RGP-2015-351). Y.F. also thanks the Japanese Government and Loughborough University for a studentship.

History

School

  • Science

Department

  • Chemistry

Published in

Organic Letters

Volume

21

Issue

12

Pages

4798-4802

Citation

FUKAZAWA, Y. ... et al, 2019. Stereoselective synthesis of atropisomeric bipyridine N,N’-dioxides by oxidative coupling. Organic Letters, 21(12), pp. 4798-4802.

Publisher

© American Chemical Society

Version

AM (Accepted Manuscript)

Publisher statement

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.9b01687.

Publication date

2019-06-05

ISSN

1523-7060

eISSN

1523-7052

Language

en

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