Carbon-Carbon Double-Bond Isomerization and Diels-Alder Reaction of Dimethyl 5-Methylene-4-isopropylidene-2-cycloheptene-1,1-dicarboxylate with Dienophiles

被引：5

作者：

Lu, Ping ^{[1
]}

Kuang, Jinqiang ^{[2
]}

Ma, Shengming ^{[1
,2
]}

机构：

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

[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, 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：

Diels-Alder reactions; isomerizations; rhodium; stereoselectivity; carbocycles; 4+2 CYCLOADDITION; CATALYST; DIPHOSPHINES;

D O I：

10.1055/s-0029-1218574

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tricyclic compounds were obtained as a single diastereomer via carbon-carbon double-bond isomerization-Diels-Alder reaction of dimethyl 5-methylene-4-isopropylidene-2-cycloheptene-1,1-dicarboxylate with dienophiles under the catalysis of [RhCl(cod)(2)](2)/dppe/AgOTf. Further experiments provided the proof of isomerization of carbon-carbon double bond. Meanwhile a sequential double Diels-Alder reaction took place without carbon carbon double-bond isomerization when 4-phenyl-4H-1,2,4-triazole-3,5-dione used as a dienophile.

引用

页码：227 / 230

页数：4

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