Regiocontrol of the palladium-catalyzed tin hydride addition to Z-enynols:: Remarkable Z-directing effects

被引：39

作者：

Hamze, Abdallah

Provot, Olivier

Brion, Jean-Daniel

Alami, Mouad

机构：

[1] Univ Paris Sud, F-92296 Chatenay Malabry, France

[2] CNRS, BioCIS, UMR 8076, Lab Chim Therapeut,Fac Pharm, F-92296 Chatenay Malabry, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 10期

关键词：

D O I：

10.1021/jo0701435

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is discussed and compared. The regioselectivity of the H-Sn bond addition was found to be controlled by the geometry of the double bond ( Z- or syn-directing effect) rather than the nature of its substituents. Exclusively alpha-vinyl stannanes were obtained from Z-enynols having various substituents on the double bond regardless of their electronic, steric, or chelating natures.

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页码：3868 / 3874

页数：7

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