Facile construction of three contiguous stereogenic centers via dynamic kinetic resolution in asymmetric transfer hydrogenation of quinolines

Mu-Wang Chen; Xian-Feng Cai; Zhang-Pei Chen; Lei Shi; Yong-Gui Zhou

doi:10.1039/c4cc06060a

Facile construction of three contiguous stereogenic centers via dynamic kinetic resolution in asymmetric transfer hydrogenation of quinolines

Chem Commun (Camb). 2014 Oct 25;50(83):12526-9. doi: 10.1039/c4cc06060a.

Authors

Mu-Wang Chen¹, Xian-Feng Cai, Zhang-Pei Chen, Lei Shi, Yong-Gui Zhou

Affiliation

¹ State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China. [email protected].

PMID: 25196398
DOI: 10.1039/c4cc06060a

Abstract

An efficient and facile route to chiral tetrahydroquinolines with three contiguous stereogenic centers via a dynamic kinetic resolution process has been successfully developed by using chiral phosphoric acid as catalyst and Hantzsch ester as the hydrogen source with up to 89% ee.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Crystallography, X-Ray
Hydrogen / chemistry
Hydrogenation
Kinetics
Models, Molecular
Phosphoric Acids / chemistry*
Quinolines / chemical synthesis*
Quinolines / chemistry
Stereoisomerism

Substances

Phosphoric Acids
Quinolines
Hydrogen
1,2,3,4-tetrahydroquinoline
phosphoric acid