Journal of Organic Chemistry p. 3028 - 3037 (1980)
Update date:2022-07-31
Topics:
Fristad, William E.
Bailey, Thomas R.
Paquette, Leo A.
Vinylsilanes are shown to be valuable synthetic intermediates in useful transformations of ketones.The epoxidation of vinylsilanes followed by lithium aluminium hydride reduction and oxidation with chromic acid and sulfuric acid in a two-phase (ether/water) system often gives high yields of 1,2-transposed ketones.With singlet oxygen and sequential sodium borohydride reduction, 2-trimethylsilyl alcohols are produced in which the α position of the parent ketone has been regiospecifically oxygenated.Fluoride ion promoted desilylation completes the conversion to the migrated allylic alcohol.
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(1979)Doi:10.1039/c3ob41878b
(2014)Doi:10.3987/com-04-10022
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(1980)
