Regio- and diastereoselective SN2' or SN2'' reactions on chiral acetals of cyclic aldehydes promoted by PhCu, BF3

Maze, Frédérique; Purpura, Martin; Bernaud, Frédéric; Mangeney, Pierre; Alexakis, Alexandre

doi:10.1016/S0957-4166(01)00319-6

Scientific article

English

Regio- and diastereoselective SN2' or SN2'' reactions on chiral acetals of cyclic aldehydes promoted by PhCu, BF3

ContributorsMaze, Frédérique; Purpura, Martin; Bernaud, Frédéric; Mangeney, Pierre; Alexakis, Alexandre

Published inTetrahedron: asymmetry, vol. 12, no. 14, p. 1957-1960

Publication date2001

Abstract

The regio- and diastereoselectivity of the addition of PhCu, BF3 reagent on chiral acetals derived from several mono or dienic aldehydes was studied. It was found that monoethylenic acetals react regio- and diastereoselectively via an overall anti SN2' reaction. The regioselectivity observed with the dienic acetals seems to be strongly dependent on the nature of the acetal. In all cases the SN2" reaction was the result of an anti process.

Affiliation entities

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

Citation (ISO format)

MAZE, Frédérique et al. Regio- and diastereoselective SN2′ or SN2″ reactions on chiral acetals of cyclic aldehydes promoted by PhCu, BF3. In: Tetrahedron: asymmetry, 2001, vol. 12, n° 14, p. 1957–1960. doi: 10.1016/S0957-4166(01)00319-6

Article

Identifiers

PID : unige:6983
DOI : 10.1016/S0957-4166(01)00319-6

Journal ISSN0957-4166

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Regio- and diastereoselective SN2' or SN2'' reactions on chiral acetals of cyclic aldehydes promoted by PhCu, BF3

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