Mechanistic insights into the gold chemistry of allenes

被引：268

作者：

Yang, Weibo ^{[1
]}

Hashmi, A. Stephen K. ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

CHEMICAL SOCIETY REVIEWS | 2014年 / 43卷 / 09期

关键词：

GOLD(I)-CATALYZED INTRAMOLECULAR HYDROARYLATION; COPPER-CATALYZED CYCLOISOMERIZATION; FACE-SELECTIVE PLATINUM; CHIRALITY TRANSFER; INTERMOLECULAR HYDROAMINATION; PROPARGYLIC ESTERS; REARRANGEMENT; (-)-CUBEBOL; 4C+3C; CYCLOADDITIONS;

D O I：

10.1039/c3cs60441a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Although most mechanistic studies on gold-catalysed reactions focused on alkynes as substrates, some knowledge about gold-catalysed conversions of allenic substrates has been obtained. This contribution summarises these insights into the reaction mechanisms of gold-catalysed transformations of allenes which are based on computational studies, labelling studies, the detection of intermediates, chirality transfer and diastereoselective product formation.

引用

页码：2941 / 2955

页数：15

共 43 条

[1] Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways [J].

Alonso, Isaac ;

Trillo, Beatriz ;

Lopez, Fernando ;

Montserrat, Sergi ;

Ujaque, Gregori ;

Castedo, Luis ;

Lledos, Agusti ;

Mascarenas, Jose L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :13020-13030

[2] Mechanistic Analysis of Gold(I)-Catalyzed Intramolecular Allene Hydroalkoxylation Reveals an Off-Cycle Bis(gold) Vinyl Species and Reversible C-O Bond Formation [J].

Brown, Timothy J. ;

Weber, Dieter ;

Gagne, Michel R. ;

Widenhoefer, Ross A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) :9134-9137

[3] Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].

Buzas, Andrea ;

Gagosz, Fabien .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615

[4] Golden carousel in catalysis: The cationic gold/propargylic ester cycle [J].

Correa, Andrea ;

Marion, Nicolas ;

Fensterbank, Louis ;

Malacria, Max ;

Nolan, Steven P. ;

Cavallo, Luigi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :718-721

[5] Synthesis of (-)-cubebol by face-selective platinum-, gold-, or copper-catalyzed cycloisomerization: Evidence for chirality transfer [J].

Fehr, Charles ;

Galindo, Jose .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (18) :2901-2904

[6] Synthesis of (-)-Cubebol by Face-Selective Platinum-, Gold-, or Copper-Catalyzed Cycloisomerization: Evidence of Chirality Transfer and Mechanistic Insights [J].

Fehr, Charles ;

Winter, Beat ;

Magpantay, Iris .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (38) :9773-9784

[7] Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].

Fuerstner, Alois ;

Davies, Paul W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449

[8] Platinum- and gold-catalyzed rearrangement reactions of propargyl acetates:: Total syntheses of (-)-α-cubebene, (-)-cubebol, sesquicarene and related terpenes [J].

Fürstner, A ;

Hannen, P .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (11) :3006-3019

[9] The role of bent acyclic allene gold complexes in axis-to-center chirality transfers [J].

Gandon, Vincent ;

Lemiere, Gilles ;

Hours, Alexandra ;

Fensterbank, Louis ;

Malacria, Max .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7534-7538

[10] Phosphoramidite Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of 3,4-Substituted Pyrrolidines [J].

Gonzalez, Ana Z. ;

Benitez, Diego ;

Tkatchouk, Ekaterina ;

Goddard, William A., III ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (14) :5500-5507

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