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
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
收藏
页码:1931 / 1934
页数:4
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