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 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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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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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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DMAP‐Catalyzed [4 + 3] Spiroannulation of Ninhydrin‐Derived MBH Carbonates with Acyclic Azadienes: Efficient Access to Multisubstituted Spiro[indanone‐azepine] Scaffolds

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

Abstract Indanedione‐containing spirocyclic derivatives are of significant interest in medicinal chemistry. However, spirofusion indanediones with seven‐membered rings remains relatively unexplored. In this study, we report an efficient DMAP‐catalyzed [4 + 3] annulation ninhydrin‐derived MBH carbonates acyclic azadienes, providing a series polysubstituted, pharmacologically interesting spiro[indanone‐azepine] good to excellent yields (up 98%) under mild conditons. The method is practical, tolerant various functional groups, and allows for the rapid synthesis diverse range products from simple, readily available starting materials. successful scale‐up reaction derivatization product further demonstrate practicality reliability method.

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 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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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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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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