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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Stereoselective Synthesis of Atropisomeric Bipyridine N,N'-Dioxides by Oxidative Coupling
Yasuaki Fukazawa1, Vladimir Yu Vaganov2, Sergei A Shipilovskikh2,3
1Department of Chemistry , Loughborough University , Loughborough LE11 3TU , U.K.
Abstract:
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.
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