Pd-Catalyzed Ligand-Directed Divergent Cycloaddition of Cyclic 1-Azadienes with Oxo-1,4-dipoles

Organic Letters, Journal Year: 2023, Volume and Issue: 25(27), P. 5011 - 5016

Published: June 29, 2023

Ligand-directed divergent synthesis (LDS) is an important synthetic tool for the preparation of structurally diverse organic molecules without tedious steps to modify substrates. Herein, we introduce realization 3,4-, 1,2-, and 1,4-cyclization benzo[d]isothiazole-1,1-dioxide-fused azadienes (BDAs) through LDS, leading tetrahydro-2H-pyrans, oxazinanes, tetrahydro-2H-1,5-oxazocines, respectively. Using phosphinooxazoline (PHOX) ligands, have developed a [4 + 2] cycloaddition between BDAs substituted 2-alkylidenetrimethylene carbonates, providing access multi-substituted chiral tetrahydro-2H-pyrans in good yields with excellent enantio-, diastereo-, regioselectivities.

Language: Английский

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Synthesis of polysubstituted spiroazepines via [4 + 3] annulation reaction of ninhydrin-derived Morita−Baylis−Hillman carbonates with 1‑heterodienes

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141478 - 141478

Published: Jan. 1, 2025

Language: Английский

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Palladium-catalyzed asymmetric [4 + 3] cycloaddition of acyclic α,β-unsaturated imines with trimethylenemethane donors: access to chiral non-fused azepines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2326 - 2331

Published: Jan. 1, 2024

An efficient approach for the construction of non-fused azepines in good yields with high enantioselectivity via Pd-catalyzed asymmetric [4 + 3] cycloaddition was developed.

Language: Английский

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Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4262 - 4267

Published: May 9, 2024

A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process C–C bond activation and intermolecular allylic substitution was well-organized. The key transformation is in situ generated hydrolysis product cyclopropenone, which triggered new with vinylethylene carbonates. mechanism investigated, demonstrating high stereoselectivity excellent atomic economy process.

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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Palladium-catalyzed (Z)-selective allylation of phosphine oxides with vinylethylene carbonates to construct phosphorus allyl alcohols

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(15), P. 3068 - 3072

Published: Jan. 1, 2024

Allylphosphine oxide compounds are important building blocks with broad applications in organic synthesis and pharmaceutical science. Herein, we report an unprecedented palladium-catalyzed allylation of phosphine oxides vinylethylene carbonates, producing various phosphorus allyl alcohols excellent yields high

Language: Английский

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Enantioselective synthesis of 8-membered lactone derivatives via organocatalytic cascade reactions

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2911 - 2916

Published: Jan. 1, 2024

The challenging 8-membered lactone derivatives bearing two vicinal chiral stereocenters were synthesized via a cascade reaction mediated by the squaramide.

Language: Английский

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Synthesis of Medium-Sized Rings by Z-Retentive Asymmetric Allylic Substitution-Enabled Intermolecular Cascade Cyclization under Iridium/Cinchona Catalysis

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(20), P. 15743 - 15750

Published: Oct. 9, 2024

Medium-sized rings are important structural units in organic molecules of significant interest. However, their efficient synthesis, especially a highly enantioselective manner, has been formidable challenge. Herein, we report an synthesis medium-sized aza-rings by Z-retentive asymmetric allylic substitution-enabled intermolecular cascade cyclization via iridium/cinchona dual catalysis. The reaction was performed under mild conditions and with good functional group tolerance. Various nine- to eleven-membered can be afforded moderate high yields (up 98%) enantioselectivities 93% ee). utilization both Z-linear dipole precursor binary catalyst is critical for the desired reactivity.

Language: Английский

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A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones: access to ten-membered N,O-containing heterocycles

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4131 - 4137

Published: Jan. 1, 2024

A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones for the synthesis ten-membered N,O-containing heterocycles is disclosed.

Language: Английский

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Palladium-Catalyzed [3 + 2] Cycloaddition of 4-Vinyl-4-Butyrolactones with Alkenes: Synthesis of Spirocyclopentane Compounds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

A palladium-catalyzed [3 + 2] cycloaddition of 4-vinyl-4-butyrolactones (VBLs) with alkenes has been developed to afford various spirocyclopentane products in high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating potential application current organic synthesis.

Language: Английский

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