Organocatalytic Asymmetric Mannich Reaction of Dihydro‐3‐carboalkoxy‐2‐quinolones with Preformed <i>N</i>‐Boc Imines

Mukhopadhyay, Soumendranath; Pan, Subhas Chandra

doi:10.1002/ejoc.201900156

Cited by 4 publications

(4 citation statements)

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“…Cinchona alkaloid obtained from thiourea catalysts, was active in this approach. The corresponding products were obtained in satisfactory yields, good to excellent ee s and moderate de s. Photocylization of an acrylanilide to form 3,4‐dihydroquinolin‐2‐ones was accomplished in good ee s [56] …”

Section: Organocatalyzed Asymmetric Mannich Reactionmentioning

confidence: 95%

“…3‐Functionalized N ‐Boc imines provided the corresponding products in good yields with moderate ee s, (Scheme 11, Table 5). [56] …”

Section: Organocatalyzed Asymmetric Mannich Reactionmentioning

confidence: 99%

“…Replacement of methyl ester with ethyl ester in dihydroquinolone, afforded the corresponding product 58 in good yield (75 % yield), 2 : 1 dr and 82 % enantioselectivity for the main diastereomer (Scheme 12). [56] …”

Section: Organocatalyzed Asymmetric Mannich Reactionmentioning

confidence: 99%

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Organocatalyzed Asymmetric Mannich Reaction: An Update

et al. 2021

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The Mannich reaction is a multicomponent reaction resulting in aminoalkylation of an acidic proton placed next to a carbonyl functional group. It involves an appropriate carbonyl compound, such as formaldehyde and a primary or secondary amine or ammonia. The final product is a β‐amino‐carbonyl compound known as a Mannich base. Reactions between aldimines and α‐methylene carbonyls are also considered as Mannich reaction since these imines are generated from the reaction of amines and aldehydes. It comprises the reaction of primary or secondary amines or ammonia, formaldehyde and appropriate α‐CH‐acidic compounds (nucleophiles) such as carbonyl compounds having α‐CH‐acidic, nitriles, acetylenes, aliphatic nitro compounds, α‐alkyl‐pyridines or imines. Owing to the development of asymmetric organocatalysis, reports on asymmetric Mannich reaction have been drastically increased. The asymmetric Mannich reaction offers access to enantioenriched β‐amino ketones or β‐amino aldehydes, which are present as a scaffold in several natural products. Organocatalysts have been developed not only as a supplement to metal‐catalyzed reactions or to biocatalysis, but nowadays, they are extensively used for the synthesis of various optically pure compounds that could not be achieved via metal‐ or biocatalyzed reactions. In this review, we try to update the advances in organocatalyzed asymmetric Mannich reactions, covering the recent advances of the subject from 2008 to date.

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Section: Organocatalyzed Asymmetric Mannich Reactionmentioning

confidence: 95%

“…3‐Functionalized N ‐Boc imines provided the corresponding products in good yields with moderate ee s, (Scheme 11, Table 5). [56] …”

Section: Organocatalyzed Asymmetric Mannich Reactionmentioning

confidence: 99%

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Organocatalyzed Asymmetric Mannich Reaction: An Update

et al. 2021

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“…An enantioselective Mannich reaction of dihydro-3-carboalkoxy-2-quinolones 176 and N-Boc imines 177 to afford biologically important 3,3-disubstituted-dihydro-2-quinolones 178 organocatalysed by squaramide catalyst 3A has been illustrated by Pan and co-workers (Scheme 59). 107 This methodology yields dihydroquinolones having an ester motif and a quaternary centre in good yields and enantioselectivities. The reaction offers simple operational procedures and further access to drugs having a 2-quinolone motif.…”

Section: Mannich Reactionsmentioning

confidence: 99%

Unravelling the Development of Non-Covalent Organocatalysis in India

Sahoo¹,

Panda²,

Sahoo³

2022

Synlett

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This review is devoted to underpinning the contributions of Indian researchers towards asymmetric organocatalysis. More specifically, a comprehensive compilation of reactions mediated by a wide range of non-covalent catalysis is illustrated. A detailed overview of vividly catalogued asymmetric organic transformations promoted by hydrogen bonding and Brønsted acid catalysis, alongside an assortment of catalysts is provided. Although asymmetric organocatalysis has etched itself in history, we aim to showcase the scientific metamorphosis of Indian research from baby steps to large strides within this field. 1 Introduction2 Non-Covalent Catalysis and Its Various Activation Modes3 Hydrogen-Bonding Catalysis3.1 Urea- and Thiourea-Derived Organocatalysts3.1.1 Thiourea-Derived Organocatalysts3.1.2 Urea-Derived Organocatalysts3.2 Squaramide-Derived Organocatalysts3.2.1 Michael Reactions3.2.2 C-Alkylation Reactions3.2.3 Mannich Reactions3.2.4 [3+2] Cycloaddition Reactions3.3 Cinchona-Alkaloid-Derived Organocatalysts3.3.1 Michael Reactions3.3.2 Aldol Reactions3.3.3 Friedel–Crafts Reactions3.3.4 Vinylogous Alkylation of 4-Methylcoumarins3.3.5 C-Sulfenylation Reactions3.3.6 Peroxyhemiacetalisation of Isochromans3.3.7 Diels–Alder Reactions3.3.8 Cycloaddition Reactions3.3.9 Morita–Baylis–Hilman Reactions4 Brønsted Acid Derived Organocatalysts4.1 Chiral Phosphoric Acid Catalysis4.1.1 Diels–Alder Reactions4.1.2 Addition of Ketimines4.1.3 Annulation of Acyclic Enecarbamates5 Conclusion

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Asymmetric epoxidation of α,β-unsaturated ketones via an amine-thiourea dual activation catalysis

Zhang

Wang

et al. 2021

Tetrahedron Letters

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Organocatalytic Asymmetric Mannich Reaction of Dihydro‐3‐carboalkoxy‐2‐quinolones with Preformed N‐Boc Imines

Cited by 4 publications

References 50 publications

Organocatalyzed Asymmetric Mannich Reaction: An Update

Organocatalyzed Asymmetric Mannich Reaction: An Update

Unravelling the Development of Non-Covalent Organocatalysis in India

Asymmetric epoxidation of α,β-unsaturated ketones via an amine-thiourea dual activation catalysis

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