Copper mediated A3-coupling reaction for the preparation of enantioselective deoxy sugar based chiral propargylamines using bifunctional ligand l-proline

Thakur, Kratima; Khare, Naveen K.

doi:10.1016/j.carres.2020.108053

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C–h Activation1

Heterobidentate No-ligands1

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2022

2024

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Cited by 5 publications

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“…Thakur and Khare 99 synthesized stereoselective chiral propargylamines 231 via the reaction among heterocyclic amine derivatives 229 , aromatic aldehyde derivatives 228 , deoxy sugar based alkyne 230 in the presence of CuI, and l -proline ( L ) in CH 3 C 6 H 5 under reflux (Scheme 95).…”

Section: C–h Activationmentioning

confidence: 99%

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Recent advances in the application of alkynes in multicomponent reactions

Hosseininezhad,

Ramazani

2024

RSC Adv.

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Section: C–h Activationmentioning

confidence: 99%

“…98 Scheme CuI-catalyzed synthesis of deoxy sugar-based chiral propargylamine derivatives. 99 Scheme Possible reaction mechanism for the synthesis of stereoselective chiral propargylamines. 99…”

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confidence: 99%

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Recent advances in the application of alkynes in multicomponent reactions

Hosseininezhad,

Ramazani

2024

RSC Adv.

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“…Recently, Khare reported an efficient three component coupling protocol of aromatic aldehyde, deoxy sugar-based alkyne (α-2-deoxy propargyl glycoside), and heterocyclic amine that yielded chiral PAs with good to excellent in a stereoselective manner [107]. The method uses CuI as the catalyst and bifunctional ligand l-proline and is applicable in many substrates (Scheme 45).…”

Section: Heterobidentate No-ligandsmentioning

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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