Metallic samarium and iodine promoted facile and efficient syntheses of trisubstituted alkenes from the acetates of Baylis-Hillman adducts

被引：25

作者：

Li, J

Hu, X

Zhang, YM

机构：

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

[2] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11790 USA

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

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 11期

基金：

高等学校博士学科点专项科研基金; 中国国家自然科学基金;

关键词：

samarium; iodine; Baylis-Hillman adduct; trisubstituted alkenes;

D O I：

10.1016/j.tetlet.2005.01.136

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Promoted by samarium metal in the presence of a catalytic amount of iodine, the Baylis-Hillman adducts underwent reductive elimination to form (E)-methylcinnamic ester derivatives. When the iodine was used in 1: 1 ratio with metallic samarium, stereospecific syntheses of allylic iodide derivatives, (2Z)-2-(iodomethyl)alk-2-enoates, were achieved. Thus, this gives a new approach to the selective construction of stereo-defined trisubstituted alkenes with the simple Sm/I-2 system. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1931 / 1934

页数：4

共 38 条

[1] NECIC ACID SYNTHONS .4. REGIOSELECTIVITY IN THE REACTIONS OF CHLORO AND IODO DERIVATIVES OF SELECTED 3-HYDROXY-2-METHYLENEALKANOATE ESTERS WITH ETHYL 2-METHYL-3-OXOBUTANOATE [J].