Synthesis and applications of chiral bis-THF in asymmetric synthesis

Alexakis, Alexandre; Tomassini, Axel; Leconte, Stéphane

doi:10.1016/j.tet.2004.07.091

Scientific article

English

Synthesis and applications of chiral bis-THF in asymmetric synthesis

ContributorsAlexakis, Alexandre; Tomassini, Axel; Leconte, Stéphane

Published inTetrahedron, vol. 60, no. 42, p. 9479-9484

Publication date2004

Abstract

The synthesis of enantiopure bis-THF is described, starting from d-mannitol. Bis-THF is used as chiral ligand for organolithium reagents in four different reactions. The enantioselectivity provided by this ligand is moderate, and the asymmetric induction is in line with the expected model.

Keywords

Asymmetric synthesis
Chirality
Diether
Organolithium reagents
Coordination

Affiliation entities

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

Citation (ISO format)

ALEXAKIS, Alexandre, TOMASSINI, Axel, LECONTE, Stéphane. Synthesis and applications of chiral bis-THF in asymmetric synthesis. In: Tetrahedron, 2004, vol. 60, n° 42, p. 9479–9484. doi: 10.1016/j.tet.2004.07.091

Article (Published version)

Identifiers

PID : unige:8112
DOI : 10.1016/j.tet.2004.07.091

Journal ISSN0040-4020

653views

0downloads

Creation21/06/2010 14:16:29

First validation21/06/2010 14:16:29

Update time14/03/2023 15:48:10

Status update14/03/2023 15:48:09

Last indexation10/06/2025 21:37:06

Archive ouverte UNIGE

Synthesis and applications of chiral bis-THF in asymmetric synthesis

The synthesis of enantiopure bis-THF is described, starting from d-mannitol. Bis-THF is used as chiral ligand for organolithium reagents in four different reactions. The enantioselectivity provided by this ligand is moderate, and the asymmetric induction is in line with the expected model.

Technical informations