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Title

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

Authors
Marek, Ilane
Mangeney, Pierre
Normant, Jean F.
Published in Tetrahedron. 1991, vol. 47, no. 9, p. 1677-1696
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.
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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. https://archive-ouverte.unige.ch/unige:8045

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