A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate:: factors influencing the yields and stereochemistry of allyl halides

被引：66

作者：

Das, B ^{[1
]}

Banerjee, J ^{[1
]}

Ravindranath, N ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2004年 / 60卷 / 38期

关键词：

Baylis-Hillman adducts; (Z)- and (E)-allyl bromides and iodides; metallic halides; NaHSO4 center dot SiO2; stereochemistry;

D O I：

10.1016/j.tet.2004.07.022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, mild and efficient stereoselective synthesis of (Z)- and (E)-allyl bromides and iodides has been developed by treatment of the Baylis-Hillman adducts with lithium bromide and iodide, respectively, in methylene chloride catalyzed by silica supported sodium hydrogen sulfate at room temperature. The role of various solvents, different reacting metallic halides, nature of the adducts and activity of several heterogeneous catalysts on the yields and stereochemistry of the products have been thoroughly studied. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8357 / 8361

页数：5

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