Diastereoselective synthesis of α-allenic alcohols from propargylic epoxides

Alexakis, Alexandre; Marek, Ilane; Mangeney, Pierre; Normant, Jean F.

doi:10.1016/S0040-4039(01)80406-8

Scientific article

Letter

English

Diastereoselective synthesis of α-allenic alcohols from propargylic epoxides

ContributorsAlexakis, Alexandre; Marek, Ilane; Mangeney, Pierre; Normant, Jean F.

Published inTetrahedron letters, vol. 30, no. 18, p. 2387-2390

Publication date1989

Abstract

The cuprocatalyzed reaction of a Grignard reagent with propargylic epoxides proceed through an addition-elimination mechanism. By changing the reaction conditions, particularly the halogen atom of RMgX it is possible to control the diastereoselectivity of the reaction. Both diastereoisomers of anf allenic alcohol can thus be obtained at will.

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Citation (ISO format)

ALEXAKIS, Alexandre et al. Diastereoselective synthesis of α-allenic alcohols from propargylic epoxides. In: Tetrahedron letters, 1989, vol. 30, n° 18, p. 2387–2390. doi: 10.1016/S0040-4039(01)80406-8

Article (Published version)

Identifiers

PID : unige:8075
DOI : 10.1016/S0040-4039(01)80406-8

Journal ISSN0040-4039

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Diastereoselective synthesis of α-allenic alcohols from propargylic epoxides

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