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Stereoselective synthesis of atropisomeric bipyridine N,N’-dioxides by oxidative coupling
journal contribution
posted on 2019-06-14, 07:53 authored by Yasuaki FukazawaYasuaki Fukazawa, Vladimir Yu Vaganov, Sergei A. Shipilovskikh, Aleksandr E. Rubtsov, Andrei MalkovAndrei MalkovBipyridine 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 LettersVolume
21Issue
12Pages
4798-4802Citation
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 SocietyVersion
- 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
2019-06-05ISSN
1523-7060eISSN
1523-7052Publisher version
Language
- en