Direct Enantioselective Three‐Component Synthesis of Optically Active Propargylamines in Water

Ohara, Mutsuyo; Hara, Yoshichika; Ohnuki, Tohru; Nakamura, Shuichi

doi:10.1002/chem.201402384

Cited by 58 publications

(23 citation statements)

References 94 publications

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“…Nakamura et al developed a bis(imidazole)pyridine (PYBIM) 42 based Cu‐catalyst to synthesize optically active propargylamines 41 in the presence of sodium dodecyl sulfate (SDS) as a surfactant (Scheme ). Propargylamines were synthesized in excellent yields with high enantiomeric excess.…”

Section: Asymmetric 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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Section: Asymmetric A3 Coupling Reactionsmentioning

confidence: 99%

Recent Advances in the A³ Coupling Reactions and their Applications

2019

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“…An enantioselective three-component reaction of aldehydes, amines, alkynes in the presence of bis(imidazoline)-Cu I catalysts in the aqueous micellar medium was reported by Ohara et al ( 2014 ) (Supplementary Table 1 , entry 8). The reactions in the presence of SDS micelles gave propargylamines ( 24 ) with much higher yields than Triton X-100, CTAB or sodium laureate.…”

Section: Miscellaneous Multicomponent Reactions Leading To Formation mentioning

confidence: 87%

Multicomponent Reactions Accelerated by Aqueous Micelles

et al. 2018

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Multicomponent reactions are powerful synthetic tools for the efficient creation of complex organic molecules in an one-pot one-step fashion. Moreover, the amount of solvents and energy needed for separation and purification of intermediates is significantly reduced what is beneficial from the green chemistry issues point of view. This review highlights the development of multicomponent reactions conducted using aqueous micelles systems during the last two decades.

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“…In 2014, pybim‐Cu(I) catalyst was successfully applied to the same reaction in aqueous media by the same group (Scheme 38, condition B). [ 89 ] The utilization of sodium dodecyl sulfate (SDS) as a surfactant enabled a homogeneous reaction mixture and the formation of a colloidal dispersion. In the presence of a slightly‐ modified ligand 43b , the A3 coupling proceeded smoothly to afford chiral propargylamines in excellent yields and enantioselectivities.…”

Section: Tridentate Imidazoline Ligandsmentioning

confidence: 99%

Chiral Imidazoline Ligands and Their Applications in Metal‐Catalyzed Asymmetric Synthesis^†

2021

Chin. J. Chem.

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As a structural analog of oxazoline, imidazoline (4,5‐dihydroimidazole) has received much attention in the rational design of chiral ligands. The additional N‐substituent provides broader space for fine‐tuning of electronic and steric effects, and it offers a good handle for immobilizing onto solid supports. In the past decades, imidazoline ring has emerged as a powerful candidate for the design of chiral nitrogen‐containing ligands, as well as a significant alternative for oxazoline ring. Various chiral imidazoline ligands have been designed and utilized in asymmetric organic reactions. These new catalysts can not only be applied in classical reactions, but also be employed to develop new organic reactions with high enantioselectivities. This review provides an overview of chiral imidazoline ligands. Their applications in asymmetric synthesis are also summarized.

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Direct Enantioselective Three‐Component Synthesis of Optically Active Propargylamines in Water

Cited by 58 publications

References 94 publications

Recent Advances in the A³ Coupling Reactions and their Applications

Recent Advances in the A³ Coupling Reactions and their Applications

Multicomponent Reactions Accelerated by Aqueous Micelles

Chiral Imidazoline Ligands and Their Applications in Metal‐Catalyzed Asymmetric Synthesis^†

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Direct Enantioselective Three‐Component Synthesis of Optically Active Propargylamines in Water

Cited by 58 publications

References 94 publications

Recent Advances in the A3 Coupling Reactions and their Applications

Recent Advances in the A3 Coupling Reactions and their Applications

Multicomponent Reactions Accelerated by Aqueous Micelles

Chiral Imidazoline Ligands and Their Applications in Metal‐Catalyzed Asymmetric Synthesis†

Contact Info

Product

Resources

About

Recent Advances in the A³ Coupling Reactions and their Applications

Recent Advances in the A³ Coupling Reactions and their Applications

Chiral Imidazoline Ligands and Their Applications in Metal‐Catalyzed Asymmetric Synthesis^†