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
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
收藏
页码:281 / 284
页数:4
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