STEREOSELECTIVE SYNTHESIS OF 1,2,4-TRIOLS VIA INTRAMOLECULAR BIS-SILYLATION OF CARBON-CARBON TRIPLE BONDS FOLLOWED BY HYDROGENATION

被引：53

作者：

MURAKAMI, M ^{[1
]}

OIKE, H ^{[1
]}

SUGAWARA, M ^{[1
]}

SUGINOME, M ^{[1
]}

ITO, Y ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT SYNTHET CHEM,YOSHIDA,KYOTO 60601,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 19期

关键词：

D O I：

10.1016/S0040-4020(01)89908-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3933 / 3946

页数：14

共 32 条

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