Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(4), P. 1175 - 1180

Published: Feb. 29, 2024

Language: Английский

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Asymmetric Substitution by Alkynyl Copper Driven Dearomatization and Rearomatization

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(47)

Published: Oct. 16, 2023

Abstract Catalytic asymmetric transformations by dearomatization have developed into a widely applicable synthetic strategy, but heavily relied on the use of arenes bearing heteroatom. In this case, is facilitated involvement p ‐orbital electron Different from conventional substrate‐dependent model, here we demonstrate that activation d transition‐metal center can serve as driving force for dearomatization, and applied to development novel alkynyl copper remote substitution reaction. A newly modified PyBox chiral ligand enables construction valuable diarylmethyl triarylmethyl skeletons in high enantioselectivities. An unexpected tandem process involving sequential substitution/cyclization/1,5‐H shift leads formation enantioenriched C−N axis. gram‐scale reaction various downstream highlight robustness method potential products. Preliminary mechanistic studies reveal mononuclear Cu‐catalyzed process.

Language: Английский

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Asymmetric copper-catalyzed alkynylallylic monofluoroalkylations with fluorinated malonates

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(31), P. 4210 - 4213

Published: Jan. 1, 2024

The unprecedented copper-catalyzed asymmetric alkynylallylic monofluoroalkylation reaction is described

Language: Английский

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Recent advances in copper-catalyzed asymmetric propargylic substitution

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100082 - 100082

Published: July 3, 2024

Language: Английский

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Synthesis of S(IV)‐Stereogenic Chiral Thio‐Oxazolidinones via Palladium‐Catalyzed Asymmetric [3+2] Annulations

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(13)

Published: Jan. 29, 2024

Organic molecules bearing chiral sulfur stereocenters exert a great impact on asymmetric catalysis and synthesis, drugs, materials. Compared with acyclic ones, the catalytic synthesis of thio-heterocycles has largely lagged behind due to lack efficient synthetic strategies. Here we establish first modular platform access thio-oxazolidinones via Pd-catalyzed [3+2] annulations vinylethylene carbonates sulfinylanilines. This protocol is featured by readily available starting materials, high enantio- diastereoselectivity. In particular, an unusual effect non-chiral supporting ligand diastereoselectivity was observed. Possible reaction mechanisms stereocontrol models were proposed.

Language: Английский

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Applications of innovative synthetic strategies in anticancer drug Discovery: The Driving Force of new chemical reactions

Bioorganic & Medicinal Chemistry Letters, Journal Year: 2025, Volume and Issue: 119, P. 130096 - 130096

Published: Jan. 9, 2025

Language: Английский

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Asymmetric Multicomponent Propargylations via Carbon Dioxide Shuttling and Fixation

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11646 - 11656

Published: July 22, 2024

Language: Английский

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Copper-Catalyzed [4+1] and [4+2] Reactions through Tandem ­Remote Propargylation/Cyclization/Isomerization with an Amine or a Hydrazine

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: March 25, 2024

Abstract Two novel copper-catalyzed cyclization reactions involving a remote propargylic substitution/cyclization/isomerization cascade are disclosed. Derivatives of the seldomly studied heterocycles thieno[2,3-c]pyrrole and thieno[2,3-d]pyridazine conveniently synthesized in moderate to good yields from primary amines or arylhydrazines through [4+1] [4+2] reactions, respectively. Preliminary mechanistic experiments corroborated occurrence designed reactions.

Language: Английский

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Copper-catalyzed asymmetric [4 + 1] annulation of yne-allylic esters with pyrazolones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110114 - 110114

Published: June 1, 2024

Language: Английский

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Dearomatization‐Rearomatization Reaction of Metal‐Polarized Aza‐ortho‐Quinone Methides

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(21)

Published: March 18, 2023

Metal-polarized aza-ortho-quinone methides (aza-o-QMs) are a unique and efficient handle for azaheterocycle synthesis. Despite great achievements, the potential of these reactive intermediates has not yet been fully exploited, especially new reaction modes. Herein, we disclosed an unprecedented dearomatization process metal-polarized aza-o-QMs, affording transient dearomatized spiroaziridine intermediates. Based on this serendipity, accomplished three sequential dearomatization-rearomatization reactions benzimidazolines with aza-sulfur ylides, enabling divergent synthesis bis-nitrogen heterocycles high efficiency flexibility. Moreover, experimental theoretical studies were performed to explain proposed mechanisms observed selectivity. Further cellular evaluation dibenzodiazepine products identified hit compound antitumor drugs.

Language: Английский

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