Organocatalytic Application of Enamine Intermediate and Hydrogen Bonding Interaction to Dissymmetric Transformation

Yao, Yuanyong; Chen, Meihang; Zhang, Xian; Xue, Wei; Bhadury, Pinaki S.

doi:10.1007/s10563-013-9162-7

Cited by 4 publications

(2 citation statements)

References 40 publications

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“…The employment of chiral hydrogen bond donors is a major activation strategy within asymmetric organocatalysis. There are several valuable reviews ,,− that highlight this subject. The most widely employed hydrogen-bonding organocatalysts include chiral-(thio)ureas, diols, phosphoric acids, and various cinchona alkaloid derivatives.…”

Section: Noncovalent Catalysismentioning

confidence: 99%

Enantioselective Organocatalyzed Transformations of β-Ketoesters

et al. 2016

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The β-ketoester structural motif continues to intrigue chemists with its electrophilic and nucleophilic sites. Proven to be a valuable tool within organic synthesis, natural product, and medicinal chemistry, reports on chiral β-ketoester molecular skeletons display a steady increase. With the reignition of organocatalysis in the past decade, asymmetric methods available for the synthesis of this structural unit has significantly expanded, making it one of the most exploited substrates for organocatalytic transformations. This review provides comprehensive information on the plethora of organocatalysts used in stereoselective organocatalyzed construction of β-ketoester-containing compounds.

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Section: Noncovalent Catalysismentioning

confidence: 99%

Enantioselective Organocatalyzed Transformations of β-Ketoesters

et al. 2016

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“…Although the activation of substrates in various Mannich‐type reactions via non‐covalent hydrogen‐bond interaction has been widely exploited , the corresponding activation of imines through ion‐pair formation has been scarcely reported. It appears that Mannich reactions catalyzed by relatively stronger Brønsted Lewis acids facilitate the nucleophilic attack of enolizable carbonyls like malonate to pi‐antibonding orbital of an sp 2 ‐hybridized carbon center of electrophilic aldimine . In the absence of a base initiator, the substrate under this reaction condition presumably undergoes activation through an ionic mechanism involving the generation of an ion‐pair.…”

Section: Introductionmentioning

confidence: 99%

Utilization of Solid Acid SO₄²⁻/TiO₂ as Catalyst to the Three‐Component Mannich Reaction at Ambient Temperature

Yao

Zhang

Chen

et al. 2017

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com). The three-component Mannich reaction of among dimethyl malonate, aromatic primary amine, and aromatic aldehyde was made successfully in the presence of solid acidic catalyst SO 4 2À /TiO 2 , with excellent catalytic activity, as compared to SO 4 2À /γ-Al 2 O 3 and SO 4 2À /ZnO. To the best of our knowledge, SO 4 2À / TiO 2 prepared at varied calcination temperatures can perform different intensities of Lewis and Brønsted acidities. Because of this point, under the optimum conditions, the effect of SO 4 2À /TiO 2 (prepared at 200°C) was much more than that of SO 4 2À /TiO 2 (prepared at 300°C or 400°C) in the three-component Mannich reaction. In observing ionization activation mode of the three-component Mannich reaction, it disclosed that the plausible mechanism possibly undergoes formation of aldimines and transformation of aldimines into β-amino esters by applying solid acidic catalyst SO 4 2À /M x O y . Dimethyl-2-((4-methylbenzo[d]thiazol-2-ylamino)(2-fluorophenyl)methyl)malonate (8). As a colorless oil, yield: 25%;1 H-NMR (500 MHz, CDCl 3 , 25°C, TMS): δ (ppm) 7.46 (t, J = 7.4 Hz, 1H), 7.39 (d, J = 8.0 Hz, 1H), 7.23-7.31 (m, 1H), 7.05 (q, J = 7.4 Hz, 3H), 6.99 (t, J = 8.0 Hz, 1H), 2526

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ChemInform Abstract: Organocatalytic Application of Enamine Intermediate and Hydrogen Bonding Interaction to Dissymmetric Transformation

et al. 2014

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Organocatalytic Application of Enamine Intermediate and Hydrogen Bonding Interaction to Dissymmetric Transformation

Cited by 4 publications

References 40 publications

Enantioselective Organocatalyzed Transformations of β-Ketoesters

Enantioselective Organocatalyzed Transformations of β-Ketoesters

Utilization of Solid Acid SO₄²⁻/TiO₂ as Catalyst to the Three‐Component Mannich Reaction at Ambient Temperature

ChemInform Abstract: Organocatalytic Application of Enamine Intermediate and Hydrogen Bonding Interaction to Dissymmetric Transformation

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Organocatalytic Application of Enamine Intermediate and Hydrogen Bonding Interaction to Dissymmetric Transformation

Cited by 4 publications

References 40 publications

Enantioselective Organocatalyzed Transformations of β-Ketoesters

Enantioselective Organocatalyzed Transformations of β-Ketoesters

Utilization of Solid Acid SO42−/TiO2 as Catalyst to the Three‐Component Mannich Reaction at Ambient Temperature

ChemInform Abstract: Organocatalytic Application of Enamine Intermediate and Hydrogen Bonding Interaction to Dissymmetric Transformation

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Utilization of Solid Acid SO₄²⁻/TiO₂ as Catalyst to the Three‐Component Mannich Reaction at Ambient Temperature