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Stereoselective synthesis of 1,2,4-triols via intramolecular bis-silylation of CarbonCarbon triple bonds followed by hydrogenation

1993; Elsevier BV; Volume: 49; Issue: 19 Linguagem: Inglês

10.1016/s0040-4020(01)89908-7

1464-5416

Masahiro Murakami, Hideaki Oike, Mitsuru Sugawara, Michinori Suginome, Yoshihiko Ito,

Organoboron and organosilicon chemistry

A new strategy for the stereoselective synthesis of 1,2,4-triols has been developed. An alkyne tethered to a disilanyl group, upon treatment with palladium acetate and tert-alkyl isocyanide, furnished an exocyclic bis-silylated olefin. Subsequent hydrogenation took place from the less-hindered side of the ring producing cis-disubstituted oxasilolane. Oxidation of the two CSi bonds of the hydrogenated oxasilolane led to the stereo- and regio-defined synthesis of 1,2,4-triol.