Gold Catalyzed Diastereoselective Cascade Allylation/Enyne Cycloisomerization to Construct Densely Functionalized Oxygen Hetereocycles

被引：30

作者：

Chen, Zili ^{[1
]}

Zhang, Yu-Xin ^{[2
]}

Wang, Ya-Hui ^{[1
]}

Zhu, Li-Li ^{[1
]}

Liu, Heng ^{[1
]}

Li, Xiao-Xiao ^{[1
]}

Guo, Lin ^{[2
]}

机构：

[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

[2] Beijing Univ Aeronaut & Astronaut, Sch Chem & Environm, Beijing 100083, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 15期

关键词：

COMPLEX POLYCYCLIC MOLECULES; ACYCLIC PRECURSORS; ENYNES; CYCLIZATION; PLATINUM; REARRANGEMENT; N-ENYNES; ACTIVATION; MECHANISM;

D O I：

10.1021/ol1012923

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new tandem allylation/enyne cycloisomerization reaction was developed to construct densely functionalized oxygen hetereocycles with high diastereoselectivities from the intermolecular reaction of allylic acetates with propargylic alcohols via gold catalysis. Terminal and nonterminal propargylic alcohols take different reaction routes either to provide 3-oxa-bicyclo[4.1.0]hept-4-ene derivatives 5 or to give endocyclic rearrangement products 7 and alkoxycyclization adducts 8. Cyclopropane's stereochemistry was mainly determined by allylic substituents.

引用

页码：3468 / 3471

页数：4

共 41 条

[1] Reorganization of enynes catalyzed by platinum salts [J].

Añorbe, L ;

Domínguez, G ;

Pérez-Castells, J .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (20) :4938-4943

[2] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[3]

Aubert C, 2006, TOP ORGANOMETAL CHEM, V19, P259

[4] A NOVEL PTCL4-CATALYZED CYCLOREARRANGEMENT OF ALLYL PROPYNYL ETHERS TO 3-OXABICYCLO[4.1.0]HEPTENES [J].

BLUM, J ;

BEERKRAFT, H ;

BADRIEH, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5567-5569

[5] Electrophilic activation and cycloisomerization of enynes: A new route to functional cyclopropanes [J].

Bruneau, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2328-2334

[6] On the mechanism of the puzzling "Endocyclic" skeletal rearrangement of 1,6-enynes [J].

Cabello, Noemi ;

Jimenez-Nunez, Eloisa ;

Bunuel, Elena ;

Cardenas, Diego J. ;

Echavarren, Antonio M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (25) :4217-4223

[7] Asymmetric Au(I)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes [J].

Chao, Chung-Meng ;

Beltrami, Denis ;

Toullec, Patrick Y. ;

Michelet, Veronique .

CHEMICAL COMMUNICATIONS, 2009, (45) :6988-6990

[8] Enyne metathesis (enyne bond reorganization) [J].

Diver, ST ;

Giessert, AJ .

CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382

[9] Non-stabilized transition metal carbenes as intermediates in intramolecular reactions of alkynes with alkenes [J].

Echavarren, AM ;

Nevado, C .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (07) :431-436

[10] Regio- and diastereoselective tandem rhodium-catalyzed allylic alkylation Pauson-Khand annulation reactions [J].

Evans, PA ;

Robinson, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4609-4610

← 1 2 3 4 5 →