Gallium-Catalyzed Domino Arylation/Oxycyclization of Allenes with Phenols

被引：12

作者：

Alcaide, Benito ^{[1
]}

Amendros, Pedro ^{[2
]}

Herrera, Fernando ^{[1
]}

Luna, Amparo ^{[1
]}

Elena de Orbe, M. ^{[1
]}

Rosario Torres, M. ^{[3
]}

机构：

[1] Univ Complutense Madrid, Grp Lactamas & Heterocidos Bioact, Dept Quim Organ 1, Unidad Asociada,CSIC,Fac Quim, E-28040 Madrid, Spain

[2] IQOG CSIC, Inst Quim Organ Gen, Madrid 28006, Spain

[3] Univ Complutense Madrid, Fac Quim, CAI Difracc Rayos X, E-28040 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 08期

关键词：

GOLD CATALYSIS; HYBRID MOLECULES; CYCLIZATION; TRANSFORMATION; REARRANGEMENT; ACTIVATION; COMPLEXITY; REACTIVITY; GOLD(III);

D O I：

10.1021/acs.joc.5b00106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of dihydrobenzofuran-appended oxindoles has been accomplished taking advantage of an unprecedented reaction between allenols and phenols under metal catalysis.

引用

页码：4157 / 4163

页数：7

共 36 条

[1] Acid-Catalyzed Synthesis of α,β-Disubstituted Conjugated Enones by a Meyer-Schuster-Type Rearrangement in Allenols [J].

Alcaide, Benito ;

Almendros, Pedro ;

Cembellin, Sara ;

Martinez del Campo, Teresa .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) :1070-1078

[2] Gold-Catalyzed Cyclization Reactions of Allenol and Alkynol Derivatives [J].

Alcaide, Benito ;

Almendros, Pedro .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (03) :939-952

[3] Unveiling the Reactivity of Propargylic Hydroperoxides under Gold Catalysis [J].

Alcaide, Benito ;

Almendros, Pedro ;

Teresa Quiros, M. ;

Lopez, Ramon ;

Menendez, Maria I. ;

Sochacka-Cwikla, Aleksandra .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (02) :898-905

[4] Direct FeX3-Based Stereocontrolled Access to (Z)-3-Alkenyl-oxindoles from Allenols [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo ;

Prieto, Natividad .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24) :11388-11392

[5] Controlled Rearrangement of Lactam-Tethered Allenols with Brominating Reagents: A Combined Experimental and Theoretical Study on α- versus β-Keto Lactam Formation [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo ;

Cembellin, Sara ;

Arno, Manuel ;

Domingo, Luis R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (41) :11559-11566

[6] Fascinating reactivity in gold catalysis: synthesis of oxetenes through rare 4-exo-dig allene cyclization and infrequent β-hydride elimination [J].

Alcaide, Benito ;

Almendros, Pedro ;

Martinez del Campo, Teresa ;

Fernandez, Israel .

CHEMICAL COMMUNICATIONS, 2011, 47 (32) :9054-9056

[7] Synthesis of Spiroheterocycles by Palladium-Catalyzed Domino Cycloisomerization/Cross-Coupling of α-Allenols and Baylis-Hillman Acetates [J].

Alcaide, Benito ;

Almendros, Pedro ;

Martinez del Campo, Teresa ;

Teresa Quiros, M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) :3344-3346

[8] Tandem Enzyme/Gold-Catalysis: From Racemic α-Allenic Acetates to Enantiomerically Enriched 2,5-Dihydrofurans in One Pot [J].

Asikainen, Martta ;

Krause, Norbert .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (14-15) :2305-2309

[9]

Ayers A.C., 1990, LIGNANS CHEM BIOL CL

[10] Highly regioselective synthesis of spirocyclic compounds by a palladium-catalyzed intermolecular tandem reaction [J].

Bi, Hai-Peng ;

Liu, Xue-Yuan ;

Gou, Ta-Rong ;

Guo, Li-Na ;

Duan, Xin-Hua ;

Shu, Xing-Zhong ;

Liang, Yong-Min .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (37) :7068-7071

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