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

✍ Scribed by Masahiro Murakami; Hideaki Oike; Mitsuru Sugawara; Michinori Suginome; Yoshihiko Ito

Book ID: 104205021
Publisher: Elsevier Science
Year: 1993
Tongue: French
Weight: 1008 KB
Volume: 49
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89908-7

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✦ Synopsis

Abstmct: A new strategy for the stereoselective synthesis of 1.2.4~uiols has been developed. An alkyne tethered to a disilanyl group, upon treatment with palladium acetate and tert-alkyl isocyanide, furnished an exocyclic bii-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 lf,4-triol. d ti 1 *t.l, 2 3

Scheme 1.

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