A<sup>3</sup>-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

Carmona, Rafaela C.; Wendler, Edison P.; Sakae, George Hideki; Comasseto, J. V.; Santos, Alcindo A. Dos

doi:10.5935/0103-5053.20140223

Cited by 6 publications

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“…Alternative approaches to propargylamines include a copper-catalyzed three-component coupling of aldehydes and alkynes using hydroxylamines as nitrogen substrates and A 3 coupling reactions using CuCl as catalyst to access propargylamine precursors of natural alkaloids . An easy approach to propargylamines via a CuI-catalyzed three-component coupling reaction with succinic acid as an additive was reported by Ren et al The authors hypothesized that the A 3 coupling reaction is driven by the formation of a succinic acid complex with the Cu(I).…”

Section: Synthesis Of Propargylaminesmentioning

confidence: 99%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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Propargylamines are a versatile class of compounds which find broad application in many fields of chemistry. This review aims to describe the different strategies developed so far for the synthesis of propargylamines and their derivatives as well as to highlight their reactivity and use as building blocks in the synthesis of chemically relevant organic compounds. In the first part of the review, the different synthetic approaches to synthesize propargylamines, such as A couplings and C-H functionalization of alkynes, have been described and organized on the basis of the catalysts employed in the syntheses. Both racemic and enantioselective approaches have been reported. In the second part, an overview of the transformations of propargylamines into heterocyclic compounds such as pyrroles, pyridines, thiazoles, and oxazoles, as well as other relevant organic derivatives, is presented.

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Section: Synthesis Of Propargylaminesmentioning

confidence: 99%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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“…In 2015, Carmona et al developed a convenient and easy protocol to access strategically functionalized hydroxy‐propargylamines through a Cu‐catalyzed A 3 coupling reaction (Scheme ) . Few representative hydroxy‐propargylamines 115a were further converted into five and six‐membered cyclic alkaloids 117 via sequential Pd‐mediated one‐pot N ‐debenzylation/triple bond reduction ( 116 ), followed by a Mitsunobu‐type cyclization (Scheme ).…”

Section: Synthetic Utility Of A3 Coupling Reactionsmentioning

confidence: 99%

Recent Advances in the A³ Coupling Reactions and their Applications

2019

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Propargylamines are an important class of organic compounds that have been widely used as building blocks for the synthesis of various kinds of chemically and biologically relevant compounds. Over the last few years, there have been a rapid growth in the research dedicated to developing the synthetic protocol for propargylamine derivatives. Among various methods that are reported for the synthesis of propargylamines, the three‐component coupling of aldehyde, amine and alkyne (commonly termed as A3 coupling reactions) secured a special place because of its convenient/atom economical approach and thus broadly used by researchers. Our aim in this review is to highlight the most recent advancement on A3 coupling reactions for the synthesis of various propargylamine derivatives as well as on the developments of subsequent transformation of these compounds to useful heterocyclic compounds and the related products.

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“…Dos Santos and co-workers demonstrated that different alkynols could be used as a substrate with a CuCl catalyst to produce the corresponding hydroxy-PAs. The resulting hydroxy-PAs were achieved in moderate to high yields and could be converted in subsequent steps to alkaloids under a simple reduction process and intramolecular cyclisation [18] (Scheme 10).…”

Section: Copper Saltsmentioning

confidence: 99%

“…It combines two unique catalytic concepts: C-H activation of the alkyne moiety and use or in situ formation of imines or enamines. Furthermore, the ideally chiral propargylamines (PA) formed by this reaction are essential precursors in organic synthesis for various products, including isoindolines [14], oxazolidines [15], pyridines [16,17], and alkaloids [18][19][20] (Scheme 2). Due to this importance, it is necessary to understand the catalyst's role and develop protocols to yield the final product in high enantiomeric excess.…”

Section: Introductionmentioning

confidence: 99%

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

2022

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The multicomponent reaction of aldehydes, amines, and alkynes, known as A3 coupling, yields propargylamines, a valuable organic scaffold, and has received significant interest and attention in the last years. In order to fully realise the potential of the metal-based catalytic protocols that facilitate this transformation, we summarise substrates, in situ and well-characterised synthetic methods that provide this scaffold and attempt a monumental classification considering several variables (Metal, Coordinating atom(s), Ligand type and name, in-situ or well-characterised, co-catalyst, catalyst and ligand Loading (mol%), solvent, volume, atmosphere, temperature, microwave, time, yield, selectivity (e.e. d.r.), substrate name, functionality, loading (amines, aldehydes, alkynes), and use of molecular sieves). This pioneering work creates a valuable database that contains 2376 entries and allows us to produce graphs and better visualise their impact on the reaction.

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A³-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

Cited by 6 publications

References 0 publications

Synthesis and Reactivity of Propargylamines in Organic Chemistry

Synthesis and Reactivity of Propargylamines in Organic Chemistry

Recent Advances in the A³ Coupling Reactions and their Applications

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

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A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

Cited by 6 publications

References 0 publications

Synthesis and Reactivity of Propargylamines in Organic Chemistry

Synthesis and Reactivity of Propargylamines in Organic Chemistry

Recent Advances in the A3 Coupling Reactions and their Applications

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

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Product

Resources

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A³-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

Recent Advances in the A³ Coupling Reactions and their Applications