Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines

Ryoichi Kuwano; Ryuhei Ikeda; Kazuki Hirasada

doi:10.1039/c5cc01971k

Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines

Chem Commun (Camb). 2015 May 1;51(35):7558-61. doi: 10.1039/c5cc01971k.

Authors

Ryoichi Kuwano¹, Ryuhei Ikeda, Kazuki Hirasada

Affiliation

¹ Department of Chemistry, Graduate School of Sciences, and International Research Center for Molecular Systems (IRCMS), Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan. rkuwano@chem.kyushu-univ.jp.

PMID: 25847758
DOI: 10.1039/c5cc01971k

Abstract

The reduction of quinolines selectively took place on their carbocyclic rings to give 5,6,7,8-tetrahydroquinolines, when the hydrogenation was conducted in the presence of a Ru(η(3)-methallyl)2(cod)-PhTRAP catalyst. The chiral ruthenium catalyst converted 8-substituted quinolines into chiral 5,6,7,8-tetrahydroquinolines with up to 91 : 9 er.