Desymmetrization of spiroactivated meso-cyclopropanes via nucleophilic substitution

Muller, Paul; Riegert, David

doi:10.1016/j.tet.2005.03.005

Scientific article

English

Desymmetrization of spiroactivated meso-cyclopropanes via nucleophilic substitution

ContributorsMuller, Paul; Riegert, David

Published inTetrahedron, vol. 61, no. 18, p. 4373-4379

Publication date2005

Abstract

The spiro-activated cyclopropane 1 undergoes desymmetrization either with Li-thiophenoxide in the presence of a chiral complexing ligand, or with ion pairs formed from thiophenols and aromatic chiral amines. The latter procedure is more efficient and provides the ring-opened thioether 6 in up to 79% yield and up to 60% ee.

Keywords

Nucleophilic substitution
Chiral ion pairs
Thiophenoxide
Chiral ligand
Chinchonine

Affiliation entities

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

Citation (ISO format)

MULLER, Paul, RIEGERT, David. Desymmetrization of spiroactivated meso-cyclopropanes via nucleophilic substitution. In: Tetrahedron, 2005, vol. 61, n° 18, p. 4373–4379. doi: 10.1016/j.tet.2005.03.005

Article

Identifiers

PID : unige:6972
DOI : 10.1016/j.tet.2005.03.005

Journal ISSN0040-4020

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Desymmetrization of spiroactivated meso-cyclopropanes via nucleophilic substitution

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