Stereoselective synthesis of atropisomeric bipyridine N,N’-dioxides by oxidative coupling
journal contributionposted on 14.06.2019 by Yasuaki Fukazawa, Vladimir Yu Vaganov, Sergei A. Shipilovskikh, Aleksandr E. Rubtsov, Andrei Malkov
Any type of content formally published in an academic journal, usually following a peer-review process.
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.
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.