New one-pot method for the stereoselective synthesis of (E)-[beta(trifluoromethylsulfonyloxy)-alkenyl](aryl) iodonium triflates.

被引：45

作者：

Kasumov, TM

Pirguliyev, NS

Brel, VK

Grishin, YK

Zefirov, NS

Stang, PJ

机构：

[1] RUSSIAN ACAD SCI,INST PHYSIOL ACT CPDS,CHERNOGOLOVKA 142432,MOSCOW REGION,RUSSIA

[2] MOSCOW MV LOMONOSOV STATE UNIV,DEPT CHEM,MOSCOW 119899,RUSSIA

[3] UNIV UTAH,DEPT CHEM,SALT LAKE CITY,UT 84112

来源：

TETRAHEDRON | 1997年 / 53卷 / 38期

关键词：

D O I：

10.1016/S0040-4020(97)00836-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of reagent 1 with acetylenes leading to the alkenyl(aryl)iodonium triflates have been investigated. The results indicate that the very simple and efficient one-pot conversion of terminal alkynes into alkenyl(aryl)iodonium triflates described in this paper presents several advantages over the previously described procedure. The stereoselectivity of these reactions is discussed on the basis of physico-chemical evidence including IR, NMR spectroscopy and X-ray analysis. It is shown thar these reactions are accompanied with anti-addition to afford (E)-[beta-(trifyloxy)alkenyl](aryl) iodonium triflates in moderate to excellent yields. A possible mechanism is also discussed. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：13139 / 13148

页数：10

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