SMI2-mediated elimination reaction of Baylis-Hillman adducts controlled by temperature:: a facile synthesis of trisubstituted alkenes and 1,5-hexadiene derivatives with E-stereoselectivity

被引：31

作者：

Li, J

Qian, WX

Zhang, YM

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2004年 / 60卷 / 27期

基金：

中国国家自然科学基金; 高等学校博士学科点专项科研基金;

关键词：

Baylis-Hillman adducts; reduction; samarium diiodide; elimination; self-coupling; trisubstituted alkene; 1,5-hexadiene derivatives; (E)-stercoselectivity;

D O I：

10.1016/j.tet.2004.04.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Promoted by samarium diiodide, the Baylis-Hillman adducts undergo hydroxyl elimination to form trisubstituted alkenes with total (E)-stereoselectivity in good to excellent yields. The flexibility of this method also opens a new route to synthesize a class of 1,5-hexadiene derivatives by temperature tuning. (C) 2004 Elsevier Ltd. All rights reserved.

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收藏

页码：5793 / 5798

页数：6

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