Tetrahedron Letters p. 1935 - 1938 (1986)
Update date:2022-08-05
Topics:
Pelter, Andrew
Colclough, M. Eamon
The reactions of 2-alkyl-1,3-dioxolan-2-ylium fluorosulphonates with trialkylalkynylborates proceed at the β-position of the alkynylborates and may be controlled to give either one or two migrations from boron to carbon.The one migration is stereospecific and the products on hydrolysis yield Z-αβ-unsaturated ketones, whilst oxidation gives specifically mono-protected 1,3-diketones.If the reactions are allowed to proceed for a longer time, then a second migration from boron to carbon occurs to yield intermediates that give other αβ-unsaturated ketones on oxidation.
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Doi:10.1039/c39860000844
(1986)Doi:10.1002/anie.201611809
(2017)Doi:10.1021/jo8013403
(2008)Doi:10.1055/s-2008-1078406
(2008)Doi:10.1016/S0040-4020(01)87565-7
(1986)Doi:10.1016/S0040-4039(00)83856-3
(1986)
