One-Pot Formation of Chiral Polysubstituted 3,4-Dihydropyrans via a Novel Organocatalytic Domino Sequence Involving Alkynal Self-Condensation

被引：29

作者：

Dong, Li-Jin ^{[1
,2
]}

Fan, Tian-Tian ^{[1
,2
]}

Wang, Chao ^{[1
]}

Sun, Jian ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Peoples R China

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

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 01期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; ASYMMETRIC-SYNTHESIS; CASCADE REACTIONS; TANDEM REACTIONS; ACCESS; 4-ISOXAZOLINES; 4H-CHROMENES; CATALYSIS; NITRONES;

D O I：

10.1021/ol3032285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The self-condensation of alkynals was for the first time implemented under mild organocatalytic conditions and was successfully linked with a domino organocatalytic inverse-electron-demand oza-Diels-Alder reaction, which led to the development of a facile one-pot method to produce a wide variety of polysubstituted chiral 3,4-dihydropyrans with good to high yields and diastereoselectivities and high enantioselectivities. The unprecedented alkynal self-condensation was revealed to pass through secondary amine-catalyzed C-C triple bond hydration and subsequent aldol condensation.

引用

页码：204 / 207

页数：4

共 45 条

[31] Recent Developments in Asymmetric Organocatalytic Domino Reactions [J].

Pellissier, Helene .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) :237-294

[32] How to make five contiguous stereocenters in one reaction: Asymmetric organocatalytic synthesis of pentasubstituted cyclohexanes [J].

Reyes, Efraim ;

Jiang, Hao ;

Milelli, Andrea ;

Elsner, Petteri ;

Hazell, Rita G. ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9202-9205

[33] Domino reactions for the synthesis of bridged bicyclic frameworks: fast access to bicyclo[n.3.1]alkanes [J].

Ruiz, Miriam ;

Lopez-Alvarado, Pilar ;

Giorgi, Giorgio ;

Carlos Menendez, J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3445-3454

[34] Inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketophosphonates catalyzed by prolinal dithioacetals [J].

Samanta, Sampak ;

Krause, Jonathan ;

Mandal, Tanmay ;

Zhao, Cong-Gui .

ORGANIC LETTERS, 2007, 9 (14) :2745-2748

[35] Enantioselective assembly of substituted dihydropyrones via organocatalytic reaction in water media [J].

Wang, Jing ;

Yu, Fang ;

Zhang, Xiaojing ;

Ma, Dawei .

ORGANIC LETTERS, 2008, 10 (12) :2561-2564

[36] Photoreactions of 1-acetylisatin with alkynes:: Regioselectivity in oxetene formation and easy access to 3-alkylideneoxindoles and dispiro[oxindole[3,2′]furan[3′,3′′]oxindole]s [J].

Wang, L ;

Zhang, Y ;

Hu, HY ;

Fun, HK ;

Xu, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3850-3858

[37] Asymmetric Organocatalytic Relay Cascades: Catalyst-Controlled Stereoisomer Selection in the Synthesis of Functionalized Cyclohexanes [J].

Wang, Yao ;

Han, Rong-Gang ;

Zhao, Yong-Long ;

Yang, Shu ;

Xu, Peng-Fei ;

Dixon, Darren J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9834-9838

[38] Proline-catalyzed direct inverse electron demand Diels-Alder reactions of ketones with 1,2,4,5-tetrazines [J].

Xie, Hexin ;

Zu, Liansuo ;

Oueis, Hanine R. ;

Wang, Hao Li Jian ;

Wang, Wei .

ORGANIC LETTERS, 2008, 10 (10) :1923-1926

[39] Organocatalytic enantioselective cascade Michael-alkylation reactions: Synthesis of chiral cyclopropanes and investigation of unexpected organocatalyzed stereoselective ring opening of cyclopropanes [J].

Xie, Hexin ;

Zu, Liansuo ;

Li, Hao ;

Wang, Jian ;

Wang, Wei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (35) :10886-10894

[40] Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Six-membered Cyclic Ketones: An Enamine/Metal Lewis Acid Bifunctional Approach [J].

Xu, Zhenghu ;

Liu, Lu ;

Wheeler, Kraig ;

Wang, Hong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (15) :3484-3488

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