Asymmetric Cyclopropanation of β,γ-Unsaturated α-Ketoesters with Stabilized Sulfur Ylides Catalyzed by C2-Symmetric Ureas

被引：69

作者：

Cheng, Ying ^{[1
]}

An, Jing ^{[1
]}

Lu, Liang-Qiu ^{[1
]}

Luo, Lan ^{[1
]}

Wang, Zheng-Yi ^{[1
]}

Chen, Jia-Rong ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 01期

基金：

中国国家自然科学基金;

关键词：

CONTAINING NATURAL-PRODUCTS; BAYLIS-HILLMAN REACTION; ENANTIOSELECTIVE CYCLOPROPANATION; ALPHA; BETA-UNSATURATED ALDEHYDES; ORGANIC-SYNTHESIS; ORGANOCATALYSIS; THIOUREA; CASCADE; DESIGN; VINYLCYCLOPROPANES;

D O I：

10.1021/jo101699r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel organocatalytic asymmetric cyclopropanation of beta,gamma-unsaturated alpha-ketoesters with stabilized sulfur ylides using C-2-symmetric urea as a hydrogen-bond catalyst has been described. This reaction allows an efficient access to 1,2,3-trisubstituted cyclopropane derivatives in moderate to good yields with up to 16:1 dr and 90: I 0 er under mild reaction conditions. The mechanism study proved that the high stereoinduction originated from the cooperative effect of the hydrogen-bond catalyst.

引用

页码：281 / 284

页数：4

共 47 条

[1] Catalytic cyclopropanation of electron deficient alkenes mediated by chiral and achiral sulfides: scope and limitations in reactions involving phenyldiazomethane and ethyl diazoacetate [J].