Rhodium(I)-Catalyzed C-C Bond Activation of Siloxyvinylcyclopropanes with Diazoesters

被引：26

作者：

Feng, Sheng ^{[1
,2
]}

Mo, Fanyang ^{[1
,2
,3
]}

Xia, Ying ^{[1
,2
]}

Liu, Zhenxing ^{[1
,2
]}

Liu, Zhen ^{[1
,2
]}

Zhang, Yan ^{[1
,2
]}

Wang, Jianbo ^{[1
,2
]}

机构：

[1] Peking Univ, BNLMS, Beijing 100871, Peoples R China

[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China

[3] Peking Univ, Coll Engn, Dept Energy & Resources Engn, Beijing 100871, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 49期

关键词：

C-C activation; carbenes; diazo compounds; rhodium; small ring systems; INTRAMOLECULAR 3+2 CYCLOADDITION; CATALYZED 5+2+1 CYCLOADDITION; NATURAL-PRODUCT SYNTHESIS; DIELS-ALDER REACTION; ENE-VINYLCYCLOPROPANES; METAL CARBENE; ALKYNES; TOSYLHYDRAZONES; INSERTION; 1ST;

D O I：

10.1002/anie.201609642

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The rhodium(I)-catalyzed C-C bond activation reaction of siloxyvinylcyclopropanes with diazoesters demonstrates a novel mode of C-C bond cleavage of siloxyvinvylcyclopanes. The alkene products were obtained as single E-configured isomers in good yields. A sigma,(3)-allyl rhodium complex, which has been previously proposed as the key intermediate in rhodium(I)-catalyzed cycloaddition of vinylcyclopropanes, has been isolated and characterized by X-ray crystallography.

引用

页码：15401 / 15405

页数：5

共 32 条

[1] FURTHER-STUDIES ON METAL-PROMOTED VINYLCYCLOPROPANE TO CYCLOPENTENE REARRANGEMENTS - STRUCTURE AND THERMOLYSIS OF RHODIUM COMPLEXES OF EXO-6-VINYLBICYCLO[3.1.0]HEX-2-ENE AND THE CRYSTAL-STRUCTURE OF THE 1,6-8-ETA-4-5-ALLYLCYCLOPENT-2-ENYL(HEXAFLUOROACETYLACETONATO)RHODIUM(III) TETRAMER [J].

ALCOCK, NW ;

BROWN, JM ;

CONNEELY, JA ;

WILLIAMSON, DH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (07) :962-971

[2]

Barluenga J., 2011, ANGEW CHEM, V123, P7626

[3] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].

Barluenga, Jose ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500

[4] PENTADIENYL METAL PHOSPHINE CHEMISTRY .20. REGIOSELECTIVE AND DIASTEREOSELECTIVE ADDITION OF ALKYL ANIONS TO ELECTRON-RICH (ETA-5-PENTADIENYL)IRON COMPLEXES [J].

BLEEKE, JR ;

WITTENBRINK, RJ ;

CLAYTON, TW ;

CHIANG, MY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6539-6545

[5] Rh(I)-Catalyzed [5+1] Cycloaddition of Vinylcyclopropanes and CO for the Synthesis of α,β- and β,γ-Cyclohexenones [J].

Jiang, Guo-Jie ;

Fu, Xu-Fei ;

Li, Qui ;

Yu, Zhi-Xiang .

ORGANIC LETTERS, 2012, 14 (03) :692-695

[6] Rh(I)-catalyzed Intramolecular [3+2] cycloaddition of trans-vinylcycloproplane-enes [J].

Jiao, Lei ;

Ye, Siyu ;

Yu, Zhi-Xiang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7178-+

[7] Vinylcyclopropane Derivatives in Transition-Metal-Catalyzed Cycloadditions for the Synthesis of Carbocyclic Compounds [J].

Jiao, Lei ;

Yu, Zhi-Xiang .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) :6842-6848

[8] Density Functional Theory Study of the Mechanisms and Stereochemistry of the Rh(I)-Catalyzed Intramolecular [3+2] Cycloadditions of 1-Ene- and 1-Yne-Vinylcyclopropanes [J].

Jiao, Lei ;

Lin, Mu ;

Yu, Zhi-Xiang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (03) :447-461

[9] Rh(I)-Catalyzed [(3+2)+1] Cycloaddition of 1-Yne/Ene-vinylcyclopropanes and CO: Homologous Pauson-Khand Reaction and Total Synthesis of (±)-α-Agarofuran [J].

Jiao, Lei ;

Lin, Mu ;

Zhuo, Lian-Gang ;

Yu, Zhi-Xiang .

ORGANIC LETTERS, 2010, 12 (11) :2528-2531

[10] Rh(I)-catalyzed intramolecular [3+2] cycloaddition reactions of 1-ene-, 1-yne- and 1-allene-vinylcyclopropanes [J].

Jiao, Lei ;

Lin, Mu ;

Yu, Zhi-Xiang .

CHEMICAL COMMUNICATIONS, 2010, 46 (07) :1059-1061

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