Asymmetric Michael reaction promoted by chiral thiazolidine-thiourea catalyst

Silva, Tiago Lima da; Rambo, Raoní Scheibler; Jacoby, Caroline Gross; Schneider, Paulo H.

doi:10.1016/j.tet.2019.130874

Cited by 11 publications

(2 citation statements)

References 28 publications

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“…The catalyst 69 exhibited higher catalytic activity for the reaction of different ketones 66 with nitroolefins 67 to give desired products 68 with an admirable yield and good to high ee at 0°C in 72 h. Also, low stereoselectivity was found for acetone when employed as a Michael donor, due to the ineffective interaction with the catalyst (Scheme 17). [64] In 2019, Tsuyoshi Miura's group developed a reliable method for the asymmetric Michael addition reaction of 5benzylfurfural derivatives 70 to nitroalkenes 71. Exploiting thiourea-pyrrolidine organocatalyst 73 with 5 mol % benzoic acid as additives, the model reaction provided nitrofuran carbaldehydes 72 in high yields and considerable enantioselectivities.…”

Section: Methodsmentioning

confidence: 99%

Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β‐Unsaturated Nitroolefins

et al. 2021

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An organocatalyzed asymmetric Michael addition reaction has been established as the most relevant and dynamic research area for the construction of chiral carbon‐carbon and carbon‐heteroatom bond. In the current scenario, rapid revolutions on asymmetric Michael addition to nitroolefins have been explored by taking advantage of newly developed chiral organocatalysts. Moreover, nitroolefins have proven as well‐known Michael acceptors for providing various structurally essential nitro‐functionalized frameworks. In addition to this, remarkable stereoselectivity has been achieved in this asymmetric process by following different mechanistic pathways that involve enamine, iminium ion intermediate formation and bifunctional H‐bonding interaction. So, we have discussed the recent advancements of organocatalytic Michael addition reactions to α, β‐unsaturated nitroolefins from the year 2016 to 2020.

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Section: Methodsmentioning

confidence: 99%

Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β‐Unsaturated Nitroolefins

et al. 2021

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“…Moreover, these derivatives are also widely used as bifunctional catalysts in combinations such as amine-thiourea and phosphine-thiourea. Along with their catalytic activity, they are also involved as a component in various reactions including guanylation, thioarylation, and C-S cross-coupling reactions [159][160][161][162][163][164][165][166].…”

Section: Thiourea Catalystmentioning

confidence: 99%

Regiodivergent Organocatalytic Reactions

et al. 2021

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Organocatalysts are abundantly used for various transformations, particularly to obtain highly enantio- and diastereomeric pure products by controlling the stereochemistry. These applications of organocatalysts have been the topic of several reviews. Organocatalysts have emerged as one of the very essential areas of research due to their mild reaction conditions, cost-effective nature, non-toxicity, and environmentally benign approach that obviates the need for transition metal catalysts and other toxic reagents. Various types of organocatalysts including amine catalysts, Brønsted acids, and Lewis bases such as N-heterocyclic carbene (NHC) catalysts, cinchona alkaloids, 4-dimethylaminopyridine (DMAP), and hydrogen bond-donating catalysts, have gained renewed interest because of their regioselectivity. In this review, we present recent advances in regiodivergent reactions that are governed by organocatalysts. Additionally, we briefly discuss the reaction pathways of achieving regiodivergent products by changes in conditions such as solvents, additives, or the temperature.

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Stereoselective Aldol and Conjugate Addition Reactions Mediated by Proline‐Based Catalysts and Its Analogues: A Concise Review

2021

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The application of amino acids and small peptides as asymmetric organocatalysts in the aldol and conjugate addition reactions is a significant breakthrough in the past decade. The desired stereoselectivity in these reactions can be attained through tunable elements of diversity present in the amino acids/peptides. On this note, the current review highlights the organocatalytic aldol and conjugate addition by proline or its analogous in the form of amide/peptide derivatives. The wide‐ranging works of literature are classified based on the use of single amino acid or peptides as a catalyst. The designing of the aforementioned amide/amino acid/peptide catalyst, including their recent applications, is also detailed. Moreover, the analogous catalysts are also discussed, embedding other hetero‐organic functionalities that mimic the catalytic activity of proline in aldol/conjugate additions.

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Asymmetric Michael reaction promoted by chiral thiazolidine-thiourea catalyst

Cited by 11 publications

References 28 publications

Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β‐Unsaturated Nitroolefins

Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β‐Unsaturated Nitroolefins

Regiodivergent Organocatalytic Reactions

Stereoselective Aldol and Conjugate Addition Reactions Mediated by Proline‐Based Catalysts and Its Analogues: A Concise Review

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