Asymmetric Synthesis of Nitrocyclopropanes Catalyzed by Chiral Primary Amines

被引：31

作者：

Dong, Li-ting ^{[1
]}

Du, Quan-sheng ^{[1
]}

Lou, Chun-liang ^{[1
]}

Zhang, Jun-min ^{[1
]}

Lu, Rui-jiong ^{[1
]}

Yan, Ming ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Ind Inst Fine Chem & Synthet Drugs, Guangzhou 510006, Guangdong, Peoples R China

来源：

SYNLETT | 2010年 / 02期

基金：

中国国家自然科学基金;

关键词：

asymmetric conjugate addition; bromonitromethane; alpha; beta-unsaturated ketone; nitrocyclopropane; organocatalysis; ENANTIOSELECTIVE CONJUGATE ADDITION; ORGANOCATALYTIC MICHAEL ADDITION; ALPHA; BETA-UNSATURATED KETONES; BIFUNCTIONAL ORGANOCATALYSTS; THIOUREA CATALYST; ORGANIC-SYNTHESIS; PEPTIDE-LACTONE; NITROALKENES; HORMAOMYCIN; DERIVATIVES;

D O I：

10.1055/s-0029-1218570

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric conjugate addition of bromonitromethane to alpha,beta-unsaturated ketones was studied using a series of chiral primary amines as the catalysts. The cascade intramolecular cyclopropanation provided nitrocyclopropanes efficiently. Excellent enantioselctivities and good yields were obtained for several cyclic enones catalyzed by a bifunctional thiourea-primary amine. Both acid and base additives were found to be necessary for the transformation.

引用

收藏

页码：266 / 270

页数：5

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