Stereoselective Synthesis of Atropisomeric Bipyridine N,N'-Dioxides by Oxidative Coupling.

Autor: Fukazawa Y; Department of Chemistry , Loughborough University , Loughborough LE11 3TU , U.K., Vaganov VY; Department of Chemistry , Perm State University , Bukireva 15 , Perm 614990 , Russia., Shipilovskikh SA; Department of Chemistry , Perm State University , Bukireva 15 , Perm 614990 , Russia.; Institute of Chemical Technology , Ural Federal University , Mira 19 , Yekaterinburg 620002 , Russia., Rubtsov AE; Department of Chemistry , Perm State University , Bukireva 15 , Perm 614990 , Russia., Malkov AV; Department of Chemistry , Loughborough University , Loughborough LE11 3TU , U.K.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2019 Jun 21; Vol. 21 (12), pp. 4798-4802. Date of Electronic Publication: 2019 Jun 05.
DOI: 10.1021/acs.orglett.9b01687
Abstrakt: 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 O 2 as a terminal oxidant. A series of 13 axially chiral bipyridine N,N'-dioxides were synthesized in up to 75% yield.
Databáze: MEDLINE