Gold(I)-Catalyzed Enantioselective Synthesis of Tetrahydrocarbazoles through Dearomative [4+2] Cycloadditions of 3/2-Substituted 2/3-Vinylindoles

被引：30

作者：

Pirovano, Valentina ^{[1
]}

Borri, Micol ^{[1
]}

Abbiati, Giorgio ^{[1
]}

Rizzato, Silvia ^{[2
]}

Rossi, Elisabetta ^{[1
]}

机构：

[1] Univ Milan, Sez Chim Gen & Organ A Marchesini, Dipartimento Sci Farmaceut, Via Venezian 21, I-20133 Milan, Italy

[2] Univ Milan, Dipartimento Chim, Via Golgi 19, I-20133 Milan, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 11期

关键词：

allenamides; asymmetric catalysis; 4+2] cycloadditions; gold; tetrahydrocarbazoles; vinylindoles; DIELS-ALDER REACTIONS; INTERMOLECULAR 2+2; GOLD CATALYSIS; FUNCTIONALIZED TETRAHYDROCARBAZOLES; MECHANISTIC INSIGHTS; ASYMMETRIC-SYNTHESIS; CASCADE REACTIONS; NATURAL-PRODUCTS; EFFICIENT ROUTE; N-ALLENAMIDES;

D O I：

10.1002/adsc.201700280

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The gold-catalyzed synthesis of tetrahydrocarbazoles through dearomative [4+2] cycloaddition reactions of 3/2-substituted 2/3-vinylindoles with allenamides is reported. In particular, we optimized the enantioselective variant of these cycloadditions. Using allenamides as dienophiles 3-substituted 2-vinylindoles gave the corresponding carbazoles with high chemo-, regio- and enantioselectivity. Good results were obtained also with 2-methyl 3-vinylindoles even if mixtures of (Z) and (E) isomers were isolated in high er and in excellent overall yields.

引用

页码：1912 / 1918

页数：7

共 61 条

[1] Diels-Alder reactions of 2-vinylindoles with open-chain C=C dienophiles [J].

Abbiati, Giorgio ;

Canevari, Valentina ;

Facoetti, Diego ;

Rossi, Elisabetta .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (03) :517-525

[2]

[Anonymous], 2008, ANGEW CHEM, V120, P2208

[3]

[Anonymous], 2008, ANGEW CHEM INT ED, V47, P2178

[4] Organocatalytic Multiple Cascade Reactions: A New Strategy for the Construction of Enantioenriched Tetrahydrocarbazoles [J].

Cao, Yi-Ju ;

Cheng, Hong-Gang ;

Lu, Liang-Qiu ;

Zhang, Ji-Ji ;

Cheng, Ying ;

Chen, Jia-Rong ;

Xiao, Wen-Jing .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (04) :617-623

[5] Enantioselective Gold(I) Catalysis with Chiral Monodentate Ligands [J].

Cera, Gianpiero ;

Bandini, Marco .

ISRAEL JOURNAL OF CHEMISTRY, 2013, 53 (11-12) :848-855

[6] Bronsted Acid Mediated Tandem Diels-Aider/Aromatization Reactions of Vinylindoles [J].

Chen, Cai-Bao ;

Wang, Xu-Fan ;

Cao, Yi-Ju ;

Cheng, Hong-Gang ;

Xiao, Wen-Jing .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) :3532-3535

[7] Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy [J].

Cowell, Joseph ;

Abualnaja, Matokah ;

Morton, Stephanie ;

Linder, Ruth ;

Buckingham, Faye ;

Waddell, Paul G. ;

Probert, Michael R. ;

Hall, Michael J. .

RSC ADVANCES, 2015, 5 (21) :16125-16152

[8] Organocatalytic Asymmetric Synthesis of Tetracyclic Pyridocarbazole Derivatives by Using a Diels-Alder/aza-Michael/Aldol Condensation Domino Reaction [J].

Enders, Dieter ;

Joie, Celine ;

Deckers, Kristina .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) :10818-10821

[9] Gold(I)-catalyzed intermolecular (4+2) cycloaddition of allenamides and acyclic dienes [J].

Faustino, Helio ;

Lopez, Fernando ;

Castedo, Luis ;

Mascarenas, Jose L. .

CHEMICAL SCIENCE, 2011, 2 (04) :633-637

[10] Axially Chiral Triazoloisoquinolin-3-ylidene Ligands in Gold(I)-Catalyzed Asymmetric Intermolecular (4+2) Cycloadditions of Allenamides and Dienes [J].

Francos, Javier ;

Grande-Carmona, Francisca ;

Faustino, Helio ;

Iglesias-Sigueenza, Javier ;

Diez, Elena ;

Alonso, Isaac ;

Fernandez, Rosario ;

Lassaletta, Jose M. ;

Lopez, Fernando ;

Mascarenas, Jose L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (35) :14322-14325

← 1 2 3 4 5 6 7 →