An Adverse Effect of Higher Catalyst Loading and Longer Reaction Time on Enantioselectivity in an Organocatalytic Multicomponent Reaction

Khopade, Tushar M.; Mete, Trimbak B.; Arora, Jyotsna S.; Bhat, Ramakrishna G.

doi:10.1002/chem.201800278

Cited by 11 publications

(4 citation statements)

References 30 publications

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“…Due to the chiral induction of the catalyst, the configuration of the product gradually stabilized, and the ee value increases. 36–38 When the reaction reaches a certain time, the product undergoes racemization due to the presence of a reversible reaction, and the ee value decreases slightly.…”

Section: Resultsmentioning

confidence: 99%

“…Due to the chiral induction of the catalyst, the configuration of the product gradually stabilized, and the ee value increases. [36][37][38] When the reaction reaches a certain time, the product undergoes racemization due to the presence of a reversible reaction, and the ee value decreases slightly. In summary, HCP(L-Pro-L-Phe-L-Phe-OMe) exhibits a fast reaction rate, high selectivity, good yield, and good adaptability, indicating its good catalytic performance in the asymmetric Michael addition and Mannich reactions.…”

Section: Paper Polymer Chemistrymentioning

confidence: 99%

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Anl-proline-modified chiral porous hyper-crosslinkedl-phenylalanine dipeptide—increased reaction rate and selectivity in asymmetric catalysis

et al. 2023

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Section: Resultsmentioning

confidence: 99%

Section: Paper Polymer Chemistrymentioning

confidence: 99%

Anl-proline-modified chiral porous hyper-crosslinkedl-phenylalanine dipeptide—increased reaction rate and selectivity in asymmetric catalysis

et al. 2023

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“…Khopade and co‐workers reported the enantioselective reaction of aldehyde 13 , ketone 163 – 164 , and Meldrum's acid 1 to produce enantiopure‐ δ ‐keto Meldrum's acid 165 – 166 (Scheme 74) wherein Cinchona‐based primary amine was used as an organocatalyst in this MCR. The mild protocol provided easy access to enantiopure carboxylic acids, esters, and amides [75] …”

Section: Synthesis Of 5‐monosubstituted Meldrum's Acidsmentioning

confidence: 99%

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

Ziarani,

Ebrahimi,

Mohajer

et al. 2023

ChemistrySelect

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Multicomponent reactions (MCRs) have gained significant attention in the field of organic synthesis due to their ability to efficiently construct complex molecular structures in a single step. Among the reagents employed in MCRs, Meldrum's acid has emerged as a highly versatile and valuable starting material, offering a wide range of molecular diversity. This comprehensive review explores the molecular diversity scope of Meldrum's acid in various MCRs, focusing on its unique attributes and the greener aspects of its application. Meldrum's acid possesses several remarkable features that contribute to its suitability as a key component in MCRs. Its high acidity enables effective participation in a variety of chemical reactions, while its rigid structure provides stability and allows for precise control of the reaction pathways. Furthermore, the ability of Meldrum's acid to undergo both nucleophilic and electrophilic attacks makes it highly versatile in the construction of diverse molecular frameworks. Its low steric hindrance further enhances its reactivity, facilitating efficient bond formation. By surveying the literature from the last five years (2018–2022), we delve into the broad range of applications of Meldrum's acid in MCRs. The review encompasses the synthesis of various heterocyclic compounds, highlighting the significance of Meldrum's acid in achieving molecular diversity. Moreover, particular emphasis is placed on the greener aspects of utilizing Meldrum's acid, considering the growing demand for environmentally friendly synthetic approaches. This includes exploring greener solvents, milder reaction conditions, and reduced waste generation.

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“…When considering enantioselective MCRs, however, there is a huge gap between homogeneous and heterogeneous catalyzed reactions. A plethora of successfully performed multicomponent syntheses under homogeneous catalysis can be found in the literature [ 178 , 186 , 205 , 206 , 207 , 208 , 209 , 210 , 211 , 212 , 213 , 214 , 215 , 216 , 217 , 218 , 219 , 220 , 221 ], whereas heterogeneous reactions are not.…”

Section: Homogeneous and Heterogeneous Catalysismentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

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An Adverse Effect of Higher Catalyst Loading and Longer Reaction Time on Enantioselectivity in an Organocatalytic Multicomponent Reaction

Cited by 11 publications

References 30 publications

Anl-proline-modified chiral porous hyper-crosslinkedl-phenylalanine dipeptide—increased reaction rate and selectivity in asymmetric catalysis

Anl-proline-modified chiral porous hyper-crosslinkedl-phenylalanine dipeptide—increased reaction rate and selectivity in asymmetric catalysis

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

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