Direct enantioselective access to 4-substituted tetrahydroquinolines by catalytic asymmetric transfer hydrogenation of quinolines

Magnus Rueping; Thomas Theissmann; Mirjam Stoeckel; Andrey P Antonchick

doi:10.1039/c1ob05870c

Direct enantioselective access to 4-substituted tetrahydroquinolines by catalytic asymmetric transfer hydrogenation of quinolines

Org Biomol Chem. 2011 Oct 7;9(19):6844-50. doi: 10.1039/c1ob05870c. Epub 2011 Aug 12.

Authors

Magnus Rueping¹, Thomas Theissmann, Mirjam Stoeckel, Andrey P Antonchick

Affiliation

¹ Institute of Organic Chemistry, RWTH Aachen University, Landoltweg, 1, D-52074, Aachen, Germany. Magnus,[email protected]

PMID: 21837348
DOI: 10.1039/c1ob05870c

Abstract

A convenient protocol for the enantioselective synthesis of 4-substituted tetrahydroquinolines has been developed. Chiral BINOL phosphoric acids promote the reduction of a wide range of 4-substituted quinolines with Hantzsch esters with good to high levels of enantioselectivity.

Publication types

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

MeSH terms

Catalysis
Crystallography, X-Ray
Hydrogenation
Models, Molecular
Molecular Structure
Quinolines / chemical synthesis*
Quinolines / chemistry*
Stereoisomerism

Substances

Quinolines