Enantioselective nucleophilic addition of organometallic reagents to quinoline: regio-, stereo- and enantioselectivity

Amiot, Franck; Cointeaux, Laure; Silve, Emmanuelle Frédérique; Alexakis, Alexandre

doi:10.1016/j.tet.2004.06.088

Scientific article

English

Enantioselective nucleophilic addition of organometallic reagents to quinoline: regio-, stereo- and enantioselectivity

ContributorsAmiot, Franck; Cointeaux, Laure; Silve, Emmanuelle Frédérique; Alexakis, Alexandre

Published inTetrahedron, vol. 60, no. 37, p. 8221-8231

Publication date2004

Abstract

Some 2-alkyl-1,2-dihydroquinoline and some 2-aryl-1,2-dihydroquinoline were obtained by enantioselective addition of methyl-, butyl-, phenyl- and 1-naphthyllithium on quinoline. Bisoxazolines were used as external chiral ligands, giving enantiomeric excess up to 79%. The ligand could be used in catalytic amounts without significant loss of enantioselectivity.

Keywords

1,2-Dihydroquinoline
Enantioselective addition
Chiral ligand
Organolithium reagents
Organometallics
Bioxazoline

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

AMIOT, Franck et al. Enantioselective nucleophilic addition of organometallic reagents to quinoline: regio-, stereo- and enantioselectivity. In: Tetrahedron, 2004, vol. 60, n° 37, p. 8221–8231. doi: 10.1016/j.tet.2004.06.088

Article (Published version)

Identifiers

PID : unige:8111
DOI : 10.1016/j.tet.2004.06.088

Journal ISSN0040-4020

691views

0downloads

Creation21/06/2010 14:16:28

First validation21/06/2010 14:16:28

Update14/03/2023 15:48:09

Status update14/03/2023 15:48:09

Last indexation10/06/2025 21:37:05

Archive ouverte UNIGE

Enantioselective nucleophilic addition of organometallic reagents to quinoline: regio-, stereo- and enantioselectivity

Technical informations