Tetrahedron p. 3073 - 3082 (1983)
Update date:2022-08-03
Topics:
Kruithof, Klaas J. H.
Schmitz, Robert F.
Klumpp, Gerhard W.
2-Lithio-2-(trimethylsilylethynyl)-1,3-dioxane 3 is prepared from 2-(trimethylsilylethynyl)-1,3-dioxane with n-BuLi.Alkylation of 3 produces propargylic ketals 2 exclusively.Reaction with group IV-B chlorotrimethylmetalanes gives both propargylic products 2 and allenes 6 depending on the solvent used.Desilylation of 2 as well as hydrolysis to the alkynyl ketones 1 can be carried out under mild conditions.The first 1-alkynyl stannyl ketone has been prepared in this way.Formation of 2-lithio-2-(3,3-dimethyl-1-butynyl)-1,3-dioxane 10 requires t-BuLi.With various electrophiles 10 yields propargylic products and/or allenes in ratios depending on the solvent used.
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Doi:10.1016/S0040-4039(00)81687-1
(1983)Doi:10.1021/jm0490686
(2005)Doi:10.1002/hlca.19830660416
(1983)Doi:10.1021/jm050256l
(2005)Doi:10.1002/ardp.19833160802
(1983)Doi:10.1021/jo051640t
(2005)
