Diastereo- and enantioselective direct vinylogous Michael addition of γ-substituted butenolides to 2-enoylpyridines catalyzed by chiral bifunctional amine-squaramides

被引：57

作者：

Wang, Zhen-Hua ^{[1
,3
]}

Wu, Zhi-Jun ^{[2
]}

Huang, Xue-Qun ^{[4
]}

Yue, Deng-Feng ^{[1
,3
]}

You, Yong ^{[1
,3
]}

Xu, Xiao-Ying ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[4] China Pharmaceut Univ, Sch Life Sci & Technol, Nanjing 211198, Jiangsu, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 87期

基金：

中国国家自然科学基金;

关键词：

CONJUGATE ADDITION; NATURAL-PRODUCTS; MANNICH REACTION; CASCADE REACTION; ALDOL REACTION; CONSTRUCTION; MUKAIYAMA; BUTYROLACTONES; CHEMISTRY;

D O I：

10.1039/c5cc06383c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The diastereo- and enantioselective direct vinylogous Michael addition reaction of gamma-substituted butenolides to 2-enoylpyridines has been achieved. A range of gamma,gamma-disubstituted butenolide derivatives, bearing two consecutive tri- and tetrasubstituted stereogenic centers, were readily obtained in good yields with excellent stereoselectivities (up to >99 : 1 dr and >99% ee).

引用

页码：15835 / 15838

页数：4

共 58 条

[1] Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid [J].

Akiyama, Takahiko ;

Honma, Yasuhiro ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :399-402

[2] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis [J].

Aleman, Jose ;

Parra, Alejandro ;

Jiang, Hao ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) :6890-6899

[3] Acetogenins from Annonaceae:: recent progress in isolation, synthesis and mechanisms of action [J].

Bermejo, A ;

Figadère, B ;

Zafra-Polo, MC ;

Barrachina, I ;

Estornell, E ;

Cortes, D .

NATURAL PRODUCT REPORTS, 2005, 22 (02) :269-303

[4] Enantioselective LaIII-pyBOX-Catalyzed Nitro-Michael Addition to (E)-2-Azachalcones [J].

Blay, Gonzalo ;

Incerti, Celia ;

Carmen Munoz, M. ;

Pedro, Jose R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (09) :1696-1705

[5] The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture [J].

Brown, SP ;

Goodwin, NC ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1192-1194

[6] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].

Casiraghi, G ;

Zanardi, F ;

Appendino, G ;

Rassu, G .

CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972

[7] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress [J].

Casiraghi, Giovanni ;

Battistini, Lucia ;

Curti, Claudio ;

Rassu, Gloria ;

Zanardi, Franca .

CHEMICAL REVIEWS, 2011, 111 (05) :3076-3154

[8] Bifunctional Amine-Squaramides: Powerful Hydrogen-Bonding Organocatalysts for Asymmetric Domino/Cascade Reactions [J].

Chauhan, Pankaj ;

Mahajan, Suruchi ;

Kaya, Ugur ;

Hack, Daniel ;

Enders, Dieter .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) :253-281

[9] Aromatic hydroxyl group-a hydrogen bonding activator in bifunctional asymmetric organocatalysis [J].

Chauhan, Pankaj ;

Chimni, Swapandeep Singh .

RSC ADVANCES, 2012, 2 (03) :737-758

[10] 3-Pyrrolyl-oxindoles as efficient nucleophiles for organocatalytic asymmetric synthesis of structurally diverse 3,3′-disubstituted oxindole derivatives [J].

Cui, Bao-Dong ;

You, Yong ;

Zhao, Jian-Qiang ;

Zuo, Jian ;

Wu, Zhi-Jun ;

Xu, Xiao-Ying ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

CHEMICAL COMMUNICATIONS, 2015, 51 (04) :757-760

← 1 2 3 4 5 6 →