A theoretical study of the nornicotine-catalyzed Mannich reaction in wet solvents and water

Yang, Sheng-Che; Lankau, Timm; Yu, Chin‐Hui

doi:10.1039/c4gc01021c

Cited by 6 publications

(2 citation statements)

References 51 publications

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“…In the first step, keto-enol tautomerism proceeds via TS1a-H 2 O and TS1b-H 2 O catalyzed by two water molecules with free energy barriers of 44.1 and 44.4 kcal mol −1 , respectively, which are close to that (41.3 kcal mol −1 ) reported previously 11. However, under the catalysis of TsOH, the free energy barriers of TS1a-TsOH and TS1b-TsOH remarkably decreased to 22.4 and 24.3 kcal mol −1 , respectively,…”

supporting

confidence: 86%

“…In the first step, keto–enol tautomerism proceeds via TS1a-H 2 O and TS1b-H 2 O catalyzed by two water molecules with free energy barriers of 44.1 and 44.4 kcal mol −1 , respectively, which are close to that (41.3 kcal mol −1 ) reported previously. 11 However, under the catalysis of TsOH, the free energy barriers of TS1a-TsOH and TS1b-TsOH remarkably decreased to 22.4 and 24.3 kcal mol −1 , respectively, showing the superior catalytic effect of TsOH over H 2 O. In the subsequent reaction of enol G1/I1 with iminium E1 , enol intermediate G1 shows higher reaction activity and product 3aa is more stable.…”

Section: Resultsmentioning

confidence: 94%

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Synthesis of pendant fullerene dimers by an aminomethylation reaction of fulleropyrrolidines bearing ketone moieties

Qin

Wang

et al. 2023

Org. Biomol. Chem.

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supporting

confidence: 86%

Section: Resultsmentioning

confidence: 94%

Synthesis of pendant fullerene dimers by an aminomethylation reaction of fulleropyrrolidines bearing ketone moieties

Qin

Wang

et al. 2023

Org. Biomol. Chem.

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On the Role of Water as a Catalyst in Prebiotic Chemistry

Saá¹,

Frontera²

2020

ChemPhysChem

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In this manuscript we provide computational support to the catalytic role of water in all kinds of pseudopericyclic reactions operating in the reductive acid cycle, as well as in other metabolic processes. Water catalysis is not limited to those reactions where simple translocation of hydrogen atoms occurs, such as those represented by NuH+E→Nu‐EH general equation. Indeed, water catalysis is more general and extremely important in tautomerization reactions of the type HX−Y=Z→X=Y−ZH, which operate in the reductive citric acid cycle and metabolic processes. Moreover, the comprehensive theoretical study reported herein illustrates that these reactions appear to behave as authentic enzyme‐catalyzed reactions showing Michaelis‐Menten behavior, however with the abnormal singularity that the concentration of the catalytic “water clusters” of different length and nature must be taken as a huge number. Overall, the results presented are suggestive of the workability of the so‐called “metabolism first” proposal in a hot water world, as water catalysis eliminates the dilution problem frequently associated to this proposal.

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Green Synthesis and Theoretical Study of β‐Amino Esters via PPh₃‐Catalyzed Mannich Reaction

et al. 2018

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A new, efficient and simple method was designed for the synthesis of novel β‐carbonyl ester derivatives by using the PPh3‐catalyzed one‐pot method, three‐component condensation from aryl amines, aryl aldehydes and dicarbonyl ester under solvent‐free conditions. The comparative results from syntheses under these conditions provide a very simple reaction procedure that produces excellent yields and high stereoselectivity, avoids column chromatographic separation and provides an easy aqueous work‐up compared with the conventional reaction. DFT calculations were utilized to confirm and understand the mechanism of the PPh3‐catalyzed Mannich reaction. Detailed analysis of the two‐reaction pathway and their energy difference proves the stereo‐selectivity effect of the Mannich reaction, favouring anti‐isomer formation.

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A theoretical study of the nornicotine-catalyzed Mannich reaction in wet solvents and water

Abstract: Quantum calculations lead the way to a green version of the versatile Mannich reaction in water catalysed by nornicotine.

Cited by 6 publications

References 51 publications

Synthesis of pendant fullerene dimers by an aminomethylation reaction of fulleropyrrolidines bearing ketone moieties

Synthesis of pendant fullerene dimers by an aminomethylation reaction of fulleropyrrolidines bearing ketone moieties

On the Role of Water as a Catalyst in Prebiotic Chemistry

Green Synthesis and Theoretical Study of β‐Amino Esters via PPh₃‐Catalyzed Mannich Reaction

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A theoretical study of the nornicotine-catalyzed Mannich reaction in wet solvents and water

Abstract: Quantum calculations lead the way to a green version of the versatile Mannich reaction in water catalysed by nornicotine.

Cited by 6 publications

References 51 publications

Synthesis of pendant fullerene dimers by an aminomethylation reaction of fulleropyrrolidines bearing ketone moieties

Synthesis of pendant fullerene dimers by an aminomethylation reaction of fulleropyrrolidines bearing ketone moieties

On the Role of Water as a Catalyst in Prebiotic Chemistry

Green Synthesis and Theoretical Study of β‐Amino Esters via PPh3‐Catalyzed Mannich Reaction

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Product

Resources

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Green Synthesis and Theoretical Study of β‐Amino Esters via PPh₃‐Catalyzed Mannich Reaction