Controllable diastereoselective cyclopropanation. enantioselective synthesis of vinylcyclopropanes via chiral telluroniurn ylides

被引：113

作者：

Liao, WW ^{[1
]}

Li, K ^{[1
]}

Tang, Y ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 43期

关键词：

D O I：

10.1021/ja036254c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel chiral telluronium salts 1 are designed for asymmetric synthesis of 1,3-disubstituted 2-vinylcyclopropanes. The allylides, generated in situ from the corresponding telluronium salt in the presence of different base, reacted with α,β-unsaturated esters, ketones, and amides to afford cis-2-silylvinyl-trans-3-substituted or trans-2-silylvinyl-trans-3-substituted cyclopropane derivatives with high diastereoselectivity and excellent enantioselectivity in good to high yields. Thus, either one of the two diastereomers could be enantioselectively synthesized at will just by the choice of LiTMP/HMPA or LDA/LiBr. The first examples of catalytic ylide reaction for enantioselective synthesis of 1,3-disubstituted 2-vinylcyclopropanes with high distereoselectivity is also achieved. Copyright © 2003 American Chemical Society.

引用

页码：13030 / 13031

页数：2

共 48 条

[1]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO

[2]

2-E

[3] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION [J].