Mechanistic details of amino acid catalyzed two-component Mannich reaction: experimental study backed by density functional calculations

Rani, Dixita; Thakur, Lalita; Khera, Mayank; Goel, Neetu; Agarwal, Jyoti

doi:10.1007/s00726-019-02798-z

Cited by 7 publications

(1 citation statement)

References 39 publications

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“…Despite many striking features, organocatalysts are seldom used in industry because of their high catalyst loading, difficulty in separation, nonrecyclability and so forth. − Even for the reduction of global chemical waste, these factors are imperative and need to be addressed rigorously. − However, catalyst immobilization can be marked as an efficient technology to produce easily separable, reusable, and aqueous catalytic systems with a high level of stereoselectivity …”

Section: Introductionmentioning

confidence: 99%

Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System

et al. 2020

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For the first time, an inclusion complex has been crafted between a carbohydrate-based molecule and a β-cyclodextrin (CD) hydrophobic cavity for asymmetric catalytic applications. This novel d-glucosamine-based inclusion compound has been synthesized in high yields using an innovative and proficient acoustic cavitation technology and well characterized using various techniques, such as infrared spectroscopy, nuclear magnetic resonance spectroscopy, ultraviolet–visible spectroscopy, thermogravimetric analysis, scanning electron microscopy, and other spectroscopic techniques. It was observed that the inclusion of a d-glucosamine derivative into the hydrophobic cavity of β-CD increased its surface area and thermal stability. This catalytic system worked well in water for the direct aldol reaction to afford the products in excellent yields with high diastereo- and enantioselectivities.

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Section: Introductionmentioning

confidence: 99%

Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System

et al. 2020

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Asymmetric Michael Addition of Unactivated Ketones with β‐Nitrostyrenes Mediated by Bifunctional L‐Prolinamide Organocatalysts

2020

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The catalytic activity of two types of L‐prolinamide organocatalysts was investigated for asymmetric Michael addition reaction of cyclic/acyclic ketones with β‐nitrostyrens. L‐Prolinamides bearing amino groups on phenyl ring worked well, though their catalytic efficiency as well as selectivity was found to be dependent upon the position of amine group to the amide bond. Organocatalyst having –NH2 group ortho to amide bond provided the best results. Substrate scope was also studied by performing the reaction of various β‐nitrostyrenes with ketones to afford the corresponding Michael adducts in excellent yields with very high diastereoselectivities and enantioselectivities in almost all cases.

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Unmodified ‘chitosan in water’ as an efficient and recyclable heterogeneous catalytic system for the synthesis of bis(indolyl)methanes

Taya,

Agarwal

2024

Applied Catalysis A: General

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Mechanistic details of amino acid catalyzed two-component Mannich reaction: experimental study backed by density functional calculations

Cited by 7 publications

References 39 publications

Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System

Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System

Asymmetric Michael Addition of Unactivated Ketones with β‐Nitrostyrenes Mediated by Bifunctional L‐Prolinamide Organocatalysts

Unmodified ‘chitosan in water’ as an efficient and recyclable heterogeneous catalytic system for the synthesis of bis(indolyl)methanes

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