ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2415 - 2423
Published: Jan. 27, 2025
Language: Английский
Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(4), P. 1175 - 1180
Published: Feb. 29, 2024
Language: Английский
Citations
21
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(4), P. 2746 - 2757
Published: Feb. 7, 2024
Remote stereocontrol in transition-metal catalysis is a challenging but interesting research topic. In this work, we achieved copper-catalyzed asymmetric yne-allylic substitution using electron-rich arenes and acyclic carbonates through remote enantioselectivity control. The reaction delivers variety of enantioenriched products that contain diverse set valuable moieties, such as conjugated enynes, indoles, indolizines, allenes, dihydrofurans, which are widely used organic synthesis act key units bioactive molecules natural products. synthetic value protocol has been demonstrated series further transformations, mechanistic studies have conducted to gain more insight into the reaction.
Language: Английский
Citations
20
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(52)
Published: Nov. 13, 2023
Impressive progress has been made in the copper-catalyzed asymmetric propargylic substitution (APS) reaction, but its use remote yne-allylic remains a challenging topic. Herein, we report first enantioselective sulfonylation of esters with sodium sulfinates. The reaction is assumed to occur via copper-vinylvinylidene species as key reactive intermediate. readily available starting materials, mild conditions, and excellent regio-, enantio- stereoselectivity, well broad substrate scope (>70 examples), show practicality attractiveness this method.
Language: Английский
Citations
28
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
Citations
23
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
Citations
12
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(12), P. 9244 - 9253
Published: June 3, 2024
Catalytic asymmetric dearomatization (CADA) is a powerful tool for the rapid construction of complex chiral three-dimensional cyclic molecules featuring quaternary carbon centers from readily available arenes. However, ubiquitous nonfunctionalized 1-naphthols to afford remains challenging and undeveloped. This study reports dearomative [4 + 1] spiroannulation via copper catalysis. reaction features highly chemo-, regio-, stereoselective nucleophilic addition intramolecular annulation cascade reactive π-extended copper-allenylidene, thus enabling practical synthesis range valuable spirocyclic enones bearing stereocenter with high efficiency. Furthermore, this protocol applicable phenols. Control experiments supported substitution-annulation mechanism by excluding process involving 1,3-sigmatropic shift. Preliminary biological activity studies indicated that synthesized hold significant promise as anticancer agents inducing tumor cell apoptosis.
Language: Английский
Citations
10
Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100082 - 100082
Published: July 3, 2024
Language: Английский
Citations
10
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1843 - 1857
Published: Jan. 1, 2024
This work summarizes recent progress in nickel-catalyzed propargylic substitution reactions, categorizing them based on the diverse types of nucleophiles involved, with a specific focus exploring asymmetric transformations.
Language: Английский
Citations
9
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(12), P. 9254 - 9264
Published: June 3, 2024
Catalytic asymmetric dearomatization reactions of α-unsubstituted β-naphthols are very challenging due to the high energy barrier resulting from loss aromaticity. Herein, we describe an example enantioselective catalytic dearomative spiroannulation with yne-allylic esters. The success this reaction relied on copper-catalyzed remote strategy using esters as bis-electrophilic reagents. This transformation features mild conditions, broad functional group tolerance, and extensive substrate scope, thereby facilitating efficient construction array enantioenriched naphthalene-2-one spiroindolenine derivatives. Experimental studies density theory calculations establish pathway origin stereoselectivity.
Language: Английский
Citations
9
Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9213 - 9218
Published: Dec. 15, 2023
Herein we employed ethynylethylene carbonates (EECs) to achieve formal [4 + 1] and [3 3] cycloaddition with cyclic 1,3-dicarbonyl compounds. On one hand, EECs styryl substitution could undergo a remotely controlled enantioselective reaction. This reaction exhibits good chemoselectivity, regioselectivity, enantioselectivity. In addition, of compounds was also achieved, leading series 4H-pyrans impressive chemoselectivity
Language: Английский
Citations
20