Diastereospecific Gold(I)‐Catalyzed Cyclization Cascade for the Controlled Preparation of N‐ and N,O‐Heterocycles

Muratore, Michael E.; Коновалов, А. И.; Armengol-Relats, Helena; Echavarren, Antonio M.

doi:10.1002/chem.201802770

Cited by 10 publications

(3 citation statements)

References 122 publications

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“…Echavarren's group subsequently expanded these studies regarding controlled preparation of N, O ‐heterocycles 38 in diastereospecific fashion from oxime‐tethered 1,6‐enynes 39 via gold(I)‐catalyzed cyclization cascade (Scheme 14). [46] The reaction offered the desired product in 71–100 % yield in presence of 2 mol% gold catalyst in dichloromethane at 65 °C for 2–18 h treatment. Electronically active arenes, polyarenes, alkanes, cycloalkanes substituted terminus oximes successfully delivered the target molecule.…”

Section: Single Cascade Reactionsmentioning

confidence: 98%

Advancements in Gold‐Catalyzed Cascade Reactions to Access Carbocycles and Heterocycles: An Overview

Ghosh

Bhakta

2022

The Chemical Record

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This review summarizes recent developments (from 2006 to 2022) in numerous important and efficient carbo-and heterocycle generations using gold-catalyzed cascade protocols. Herein, methodologies involve selectivity, cost-effectiveness, and ease of product formation being controlled by the ligand as well as the counter anion, catalyst, substrate, and reaction conditions. Gold-catalyzed cascade reactions covered different strategies through the compilation of various approaches such as cyclization, hydroarylation, intermolecular and intramolecular cascade reactions, etc. This entitled reaction is also useful for the synthesis of spiro, fused, bridged carbo-and heterocycles.

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Section: Single Cascade Reactionsmentioning

confidence: 98%

Advancements in Gold‐Catalyzed Cascade Reactions to Access Carbocycles and Heterocycles: An Overview

Ghosh

Bhakta

2022

The Chemical Record

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“…Our group also discovered the cyclization of 1,n-enynes 10 possessing a carbonyl group, giving oxatricyclic compounds 11 by a formal [2+2+2] alkyne/alkene/carbonyl cycloaddition cascade (Scheme 5). [16][17][18] These reactions take place via intramolecular nucleophilic attack of the ketone in cyclopropyl gold(I) carbene XII to deliver oxonium cations XIII stereospecifically. Next, intermediate XIII undergoes a Prins-type cyclization forming tertiary carbocations XIV.…”

Section: Short Review Synthesismentioning

confidence: 99%

Assembling Complex Structures through Cascade and Cycloaddition Processes via Non-Acceptor Gold or Rhodium Carbenes

et al. 2021

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The ability of highly energetic metal-carbene intermediates to engage in complex cascade or formal-cycloaddition processes is one of the most powerful tools for building intricate molecular architectures in a straightforward manner. Among this type of organometallic intermediates, non-acceptor metal carbenes are particularly challenging to access and, therefore, have experienced a slower development. In this regard, our group has exploited the use of electrophilic gold(I) complexes to selectively activate certain classes of substrates and generate this type of intermediates. Thus, very different type of molecules, such as enynes or 7-substituted cyclohepatrienes, lead to the formation of carbenes under gold(I) catalysis. Related rhodium(II) carbenes can also be generated from cyclohepatrienes. In this account, we aim to summarize our efforts towards the in-situ generation of these highly versatile organometallic species, and the study of their reactivity through formal cycloadditions or complex cascade reactions.

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“…The Z orientation at the C=N bond of the oxime group is determining to obtain 133 , otherwise, with the E -oxime variant, dihydropyrrole N -oxides are isolated. The latter substrates resulted from the initial N -attack of the oxime over the gold-carbene intermediate (Muratore et al, 2018).…”

Section: Gold-catalyzed Isomerization Processes Involving An Initimentioning

confidence: 99%

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

2019

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Gold is currently one of the most used metals in organometallic catalysis. The ability of gold to activate unsaturated groups in different modes, together with its tolerance to a wide range of functional groups and reaction conditions, turns gold-based complexes into efficient and highly sought after catalysts. Natural products and relevant compounds with biological and pharmaceutical activity are often characterized by complex molecular structures. (Cyclo)isomerization reactions are often a useful strategy for the generation of this molecular complexity from synthetically accessible reactants. In this review, we collect the most recent contributions in which gold(I)- and/or gold(III)-catalysts mediate intramolecular (cyclo)isomerization transformations of unsaturated species, which commonly feature allene or alkyne motifs, and organize them depending on the substrate and the reaction type.

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Diastereospecific Gold(I)‐Catalyzed Cyclization Cascade for the Controlled Preparation of N‐ and N,O‐Heterocycles

Cited by 10 publications

References 122 publications

Advancements in Gold‐Catalyzed Cascade Reactions to Access Carbocycles and Heterocycles: An Overview

Advancements in Gold‐Catalyzed Cascade Reactions to Access Carbocycles and Heterocycles: An Overview

Assembling Complex Structures through Cascade and Cycloaddition Processes via Non-Acceptor Gold or Rhodium Carbenes

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

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