Catalytic Enantioselective α-Allylation of Deconjugated Butenolides with Aza-π-allylpalladium 1,4-Dipoles: Access to Optically Pure 2-Piperidones Bearing an All-Carbon Quaternary Stereocenter

Organic Letters, Journal Year: 2022, Volume and Issue: 24(45), P. 8348 - 8353

Published: Nov. 10, 2022

A palladium-catalyzed enantioselective α-allylation of deconjugated butenolides with aza-π-allylpalladium 1,4-diploes, in situ generated from palladium-mediated decarboxylation cyclic carbamates and amide-substituted acyclic carbonates, has been successfully developed. An array enantioenriched 2-piperidones bearing an all-carbon quaternary stereocenter were obtained high yields excellent enantioselectivities (up to 99% yield ee). The utility this method was also showcased by a large-scale reaction synthetic transformations the product.

Language: Английский

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Enantioselective synthesis of spirooxindole-pyran derivatives via a remote inverse-electron-demand Diels–Alder reaction of β,γ-unsaturated amides

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(16), P. 3198 - 3203

Published: Jan. 1, 2024

Novel construction methods for obtaining 3,4'-pyran spirooxindole heterocyclic skeletons have always been the focus of attention. Herein, we report a highly enantioselective inverse-electron-demand oxa-Diels-Alder cycloaddition reaction β,γ-unsaturated pyrazole amide and

Language: Английский

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Advances in chromone-based reactants in the ring opening and skeletal reconstruction reaction: access to skeletally diverse salicyloylbenzene/heterocycle derivatives

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(23), P. 4681 - 4698

Published: Jan. 1, 2022

Salicyloylbenzene/heterocycles are privileged scaffolds found in many natural products and bioactive molecules. Numerous useful approaches for the preparation of these have been developed recent years. Among approaches, chromone-based reactants demonstrated their importance synthesis salicyloylbenzene/heterocycle with structural complexity potential biological appeal. In this review, advances salicyloylbenzene/heterocycles summarized discussed according to which could be achieved one step via ring-opening skeletal reconstruction reactions. Both mechanisms applications corresponding organic medicinal chemistry also described.

Language: Английский

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Recent advances in the synthesis of benzo[b]thiophene fused polycyclic derivatives: Strategies and reactions

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(6), P. 108003 - 108003

Published: Nov. 13, 2022

Language: Английский

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Palladium-catalyzed [6 + 4] cycloaddition with π-allyl all-carbon 1,6-dipole for the synthesis of ten-membered heterocycles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(5), P. 1299 - 1304

Published: Dec. 25, 2023

This work introduces a novel α,α-diester-δ-vinylvalerolactone as dipolar precursor in palladium-catalyzed [6 + 4] cycloaddition reaction with azadienes, resulting the production of ten-membered heterocycles.

Language: Английский

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Enantioselective construction of dihydropyranone-fused indoles by [3 + 3] annulation of in situ-derived indolin-3-ones and unsaturated carboxylic esters

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(11), P. 2740 - 2745

Published: Jan. 1, 2023

This work discloses an N-heterocyclic carbene (NHC) and base-mediated [3 + 3] annulation reaction of unsaturated carboxylic esters sulfonium salts for rapid direct access to enantioselective dihydropyrano[3,2- b ]indoles.

Language: Английский

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A combination of polarity reversal, Diels–Alder cycloaddition and skeletal remodeling to access pyridine-fused nitrones

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(30), P. 4775 - 4778

Published: Jan. 1, 2022

An unprecedented cascade strategy consisting of polarity reversal, normal electron-demand Diels-Alder cycloaddition and skeletal remodeling was developed to construct novel pyridine-fused nitrones in up 82% yield. The key the success umpolung process, which transformed electron-deficient 3-nitropyridinium ring into a reactive, π-extended cyclic nitroalkene, serving as rarely reported hetero-diene participate cycloadditions.

Language: Английский

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Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(12), P. 3130 - 3168

Published: Jan. 1, 2023

This review summarizes a view of the advances in catalytic asymmetric α-functionalization vinylogous nucleophilic species, content which is categorized based on type donor.

Language: Английский

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Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins

Molecules, Journal Year: 2023, Volume and Issue: 28(11), P. 4410 - 4410

Published: May 29, 2023

[3 + 2] Cycloaddition reactions of heteroaromatic N-ylides with electron-deficient olefins have been developed. The N-ylides, in situ generated from N-phenacylbenzothiazolium bromides, can smoothly react maleimides under very mild conditions, affording fused polycyclic octahydropyrrolo[3,4-c]pyrroles good-to-excellent isolated yields. This reaction concept could also be extended to 3-trifluoroethylidene oxindoles and benzylidenemalononitriles as for accessing highly functionalized polyheterocyclic compounds. A gram-scale experiment was carried out verify the practicability methodology.

Language: Английский

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Chiral phosphoric acid-catalyzed enantioselective synthesis of functionalized pyrrolinones containing a geminal diamine core via an aza-Friedel–Crafts reaction of newly developed pyrrolinone ketimines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1437 - 1443

Published: Jan. 1, 2024

A class of novel pyrrolinone ketimines was synthesized for the first time and applied to asymmetric aza-Friedel–Crafts reaction with phenolic compounds.

Language: Английский

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