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Scientific article
English

Diastereoselective syn or anti opening of propargylic epoxides. Synthesis of α-allenic alcohols

Published inTetrahedron, vol. 47, no. 9, p. 1677-1696
Publication date1991
Abstract

Propargylic epoxides easily react with Grignard reagents and catalytic amounts of copper(I) salt to afford a-allenic alcohols. The reaction is highly diastereoselective and its stereochemical outcome (syn or anti isomer) can be fully controlled. The syn diastereomer, probably arising through an addition-elimination mechanism, is better obtained with RMgCl and copper(I) bromide, whereas the anti diastereomer, is better obtained with RMgBr and a complexed copper(I) salt. With RLi and a catalytic amount of copper salt, phenethynyl cyclohexene oxide reacts through reductive lithition, affording, stereoselectivety, an allenyl lithium reagent.

Affiliation Not a UNIGE publication
Citation (ISO format)
ALEXAKIS, Alexandre et al. Diastereoselective syn or anti opening of propargylic epoxides. Synthesis of α-allenic alcohols. In: Tetrahedron, 1991, vol. 47, n° 9, p. 1677–1696. doi: 10.1016/S0040-4020(01)96911-X
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ISSN of the journal0040-4020
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