Journal of the Chemical Society. Perkin transactions I p. 3419 - 3430 (1992)
Update date:2022-08-04
Topics: Stereochemistry Elimination
Kocienski, Philip J.
Pritchard, Martin
Wadman, Sjoerd N.
Whitby, Richard J.
Yeates, Clive L.
5-Alkyl-2,3-dihydrofurans 3a-j prepared by the alkylation of 5-lithio-2,3-dihydrofuran 2 with primary alkyl bromides and iodides, undergo Ni(0)-catalysed coupling with Grignard reagents to give homoallylic alcohols.The yield and stereoselectivity depend on the structure of the Grignard reagent with the best results being obtained with long chain primary Grignard reagents and Grignard reagents lacking β-hydrogens (Me, Ph, Me3SiCH2). 5-(1-Hydroxyalkyl)-2,3-dihydrofurans 20 and 21 are poor substrates for the coupling reaction.Mechanisms are proposed for the coupling as well as competing reduction and isomerisation reactions.
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