Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison

Gonçalves, Maria-Héléna; Martinez, Alexandre; Grass, Stéphane; Page, Philip C. Bulman; Lacour, Jérôme

doi:10.1016/j.tetlet.2006.05.132

Scientific article

English

Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison

ContributorsGonçalves, Maria-Héléna; Martinez, Alexandre; Grass, Stéphane; Page, Philip C. Bulman; Lacour, Jérôme

Published inTetrahedron letters, vol. 47, no. 30, p. 5297-5301

Publication date2006

Abstract

Homologous biphenyl and (diastereomeric) binaphthyl tertiary azepines and quaternary iminium salts were prepared from (+)-(S,S)-l-acetonamine. Both the amines and iminium ions behave as effective catalysts for the enantioselective epoxidation of unfunctionalized olefins (ee up to 83%).

Affiliation entities

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

Citation (ISO format)

GONÇALVES, Maria-Héléna et al. Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison. In: Tetrahedron letters, 2006, vol. 47, n° 30, p. 5297–5301. doi: 10.1016/j.tetlet.2006.05.132

Article

Identifiers

PID : unige:7059
DOI : 10.1016/j.tetlet.2006.05.132

Journal ISSN0040-4039

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Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison

Homologous biphenyl and (diastereomeric) binaphthyl tertiary azepines and quaternary iminium salts were prepared from (+)-(S,S)-l-acetonamine. Both the amines and iminium ions behave as effective catalysts for the enantioselective epoxidation of unfunctionalized olefins (ee up to 83%).

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