Rh(I)-Catalyzed Formal [5+1]/[2+2+1] Cycloaddition of 1-Yne-vinylcyclopropanes and Two CO Units: One-Step Construction of Multifunctional Angular Tricyclic 5/5/6 Compounds

被引：80

作者：

Lin, Mu ^{[1
]}

Li, Feng ^{[1
]}

Jiao, Lei ^{[1
]}

Yu, Zhi-Xiang ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 06期

关键词：

PAUSON-KHAND REACTION; CARBONYLATIVE CARBOTRICYCLIZATION; ATOM ECONOMY; ENEDIYNES; MECHANISM; CATALYSIS; ALKYNES;

D O I：

10.1021/ja110039h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel Rh(I)-catalyzed formal [5 + 1]/[2 + 2 + 1] cycloaddition of 1-yne-vinylcydopropanes and two CO units for the construction of multifunctional angular tricyclic 5/5/6 skeletons with one or two adjacent bridgehead quaternary all-carbon stereocenters in one step has been developed. Preliminary density functional theory calculations have been carried out to investigate the reaction mechanism and the substituent effects.

引用

页码：1690 / 1693

页数：4

共 32 条

[1] Silicon-initiated carbonylative carbotricyclization and [2+2+2+1] cycloaddition of enediynes catalyzed by rhodium complexes [J].

Bennacer, B ;

Fujiwara, M ;

Lee, SY ;

Ojima, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17756-17767

[2] Novel [2+2+2+1] cycloaddition of enediynes catalyzed by rhodium complexes [J].

Bennacer, B ;

Fujiwara, M ;

Ojima, I .

ORGANIC LETTERS, 2004, 6 (20) :3589-3591

[3] Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO [J].

Brancour, Celia ;

Fukuyama, Takahide ;

Ohta, Yuko ;

Ryu, Ilhyong ;

Dhimane, Anne-Lise ;

Fensterbank, Louis ;

Malacria, Max .

CHEMICAL COMMUNICATIONS, 2010, 46 (30) :5470-5472

[4] Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].

Brummond, KM ;

Kent, JL .

TETRAHEDRON, 2000, 56 (21) :3263-3283

[5] Sequential homobimetallic catalysis: an unprecedented tandem Pd(0)-catalysed deprotection - Pd(II)-catalysed heterocyclisation reaction leading to benzofurans [J].

Gabriele, B ;

Mancuso, R ;

Salerno, G ;

Veltri, L .

CHEMICAL COMMUNICATIONS, 2005, (02) :271-273

[6] A novel palladium-catalyzed dicarbonylation process leading to coumarins [J].

Gabriele, Bartolo ;

Mancuso, Raffaella ;

Salerno, Giuseppe ;

Plastina, Pierluigi .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (02) :756-759

[7] The Pauson-Khand reaction: the catalytic age is here! [J].

Gibson, SE ;

Stevenazzi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (16) :1800-1810

[8] Rhodium-catalyzed [2+2+1+1] cyclocarbonylative coupling of Alkynes with carbon monoxide affording tetrasubstituted p-benzoquinones [J].

Huang, Qiufeng ;

Hua, Ruimao .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (29) :8333-8337

[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] Carbonylative [5+1] cycloaddition of cyclopropyl imines catalyzed by ruthenium carbonyl complex [J].

Kamitani, A ;

Chatani, N ;

Morimoto, T ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9230-9233

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