Enantioselective Construction of [6,5,6]-Carbocyclic Systems by Organo/Metal-Catalyzed Sequential Reactions

被引：14

作者：

Wu, Xiang ^{[1
]}

Li, Ming-Li

Chen, Dian-Feng

Chen, Shu-Sen

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 10期

基金：

中国博士后科学基金;

关键词：

DIELS-ALDER REACTIONS; GIBBERELLIC-ACID; GOLD CATALYSIS; ALPHA; BETA-UNSATURATED KETONES; TRANSITION-METAL; AMINE CATALYSIS; TAIWANIAQUINOIDS; ROUTE; (+/-)-TAIWANIAQUINOL-B; (+/-)-DICHROANAL-B;

D O I：

10.1021/jo5006729

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient strategy for the enantioselective construction of [6,5,6]-carbocyclic compounds has been established via one-pot reaction of (E)-4-(2-ethynylphenyl)but-3-en-2-ones with maleimide sequentially catalyzed by cinchona alkaloid-based primary amine and gold complex (Ph3PAuNTf2). This methodology provided a facile approach to access the [6,5,6]-tricyclic skeleton in fairly good yield and with perfect enantioselectivities (98% to >99% ee).

引用

页码：4743 / 4750

页数：8

共 68 条

[31] Merging Organocatalysis and Gold Catalysis: Enantioselective Synthesis of Tetracyclic Indole Derivatives through a Sequential Double Friedel-Crafts Type Reaction [J].

Loh, Charles C. J. ;

Badorrek, Jan ;

Raabe, Gerhard ;

Enders, Dieter .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (48) :13409-13414

[32] GENERAL STRATEGY FOR GIBBERELLIN SYNTHESIS - TOTAL SYNTHESES OF (+/-)-GIBBERELLIN-A1(1) AND GIBBERELLIC-ACID [J].

LOMBARDO, L ;

MANDER, LN ;

TURNER, JV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) :6626-6628

[33] The Taiwaniaquinoids: A Review [J].

Majetich, George ;

Shimkus, Joel M. .

JOURNAL OF NATURAL PRODUCTS, 2010, 73 (02) :284-298

[34] Concise syntheses of (±)-dichroanone, (±)-dichroanal B, (±)-taiwaniaquinol B, and (±)-taiwaniaquinone D [J].

Majetich, George ;

Shimkus, Joel M. .

TETRAHEDRON LETTERS, 2009, 50 (26) :3311-3313

[35]

Martin GC., 1983, The biochemistry and Physiology of gibberellins Crozier, V2, P395

[36] The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone [J].

McFadden, Ryan M. ;

Stoltz, Brian M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (24) :7738-7739

[37] Cinchona-based Primary Amine Catalysis in the Asymmetric Functionalization of Carbonyl Compounds [J].

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) :9748-9770

[38] Asymmetric One-Pot Sequential Organo- and Gold Catalysis for the Enantioselective Synthesis of Dihydropyrrole Derivatives [J].

Monge, David ;

Jensen, Kim L. ;

Franke, Patrick T. ;

Lykke, Lennart ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (31) :9478-9484

[39] Enantioselective metallo-organocatalyzed preparation of cyclopentanes bearing an all-carbon quaternary stereocenter [J].

Montaignac, Benjamin ;

Praveen, Chandrasekaran ;

Vitale, Maxime R. ;

Michelet, Veronique ;

Ratovelomanana-Vidal, Virginie .

CHEMICAL COMMUNICATIONS, 2012, 48 (52) :6559-6561

[40] Copper(I)-amine metallo-organocatalyzed synthesis of carbo- and heterocyclic systems [J].

Montaignac, Benjamin ;

Oestlund, Victor ;

Vitale, Maxime R. ;

Ratovelomanana-Vidal, Virgnie ;

Michelet, Veronique .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (11) :2300-2306

← 1 2 3 4 5 6 7 →