Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings

Alexakis, Alexandre; Vrancken, Emmanuel; Mangeney, Pierre

doi:10.1039/b005474g

Scientific article

English

Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings

ContributorsAlexakis, Alexandre; Vrancken, Emmanuel; Mangeney, Pierre

Published inJournal of the Chemical Society. Perkin transactions 1, no. 20, p. 3354-3355

Publication date2000

Abstract

Cyclooctene oxide 1, cycloocta-1,3-diene oxide 4, and cycloocta-1,5-diene oxide 7 react with organolithium reagents by nucleophilic opening or a- or ß-deprotonation. The addition of BF3·Et2O affects the course of the reaction, and also strongly accelerates it. If (–)-sparteine is present, a moderate to high asymmetric induction is obtained.

Affiliation

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

Citation (ISO format)

ALEXAKIS, Alexandre, VRANCKEN, Emmanuel, MANGENEY, Pierre. Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings. In: Journal of the Chemical Society. Perkin transactions 1, 2000, n° 20, p. 3354–3355. doi: 10.1039/b005474g

Article (Published version)

Identifiers

PID : unige:8218
DOI : 10.1039/b005474g

ISSN of the journal1364-5463

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Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings

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