Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
The palladium-catalyzed [3 + 2] decarboxylative cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines has been developed, providing the sulfamate-fused pyrrolidine derivatives in high yields good diastereoselectivities.
Язык: Английский
Chemical Science, Год журнала: 2023, Номер 14(11), С. 3024 - 3029
Опубликована: Янв. 1, 2023
Inspired by a fungicide, we designed 5-vinyloxazolidine-2,4-diones as new precursors of π-allylpalladium zwitterionic intermediates and developed palladium-catalyzed asymmetric (5 + 3) cycloaddition with azomethine imines (3 2) 1,1-dicyanoalkenes. Both reactions proceeded smoothly under mild reaction conditions to produce various chiral heterocyclic compounds in high yields excellent enantioselectivities. These results revealed that were type suitable precursor for palladium catalysis will find extensive applications Pd-catalyzed such allylic alkylation.
Язык: Английский
Процитировано
27
Chinese Chemical Letters, Год журнала: 2023, Номер 34(11), С. 108401 - 108401
Опубликована: Март 30, 2023
Язык: Английский
Процитировано
25
ACS Catalysis, Год журнала: 2024, Номер 14(13), С. 9940 - 9954
Опубликована: Июнь 19, 2024
Metal-catalyzed allenylic substitution reactions where allenes serve as electrophilic precursors have been recognized a rapid way for novel allene construction. On the contrary, chemistry in which act nucleophiles has far less investigated, especially powerful platform such metal-catalyzed allylic alkylation reactions. We herein describe two unprecedented palladium-catalyzed of an nucleophile. In first reaction, using vinyloxazolidinones allyl precursor, asymmetric allylation trisubstituted allenones worked well to prepare array axially chiral tetrasubstituted allenes. Mechanistic studies and density functional theory (DFT) calculations indicated that weak hydrogen-bonding interaction between acidic C(sp2)–H allenone nitrogen anion π-azaallyl-Pd species is key success stereocontrol. This reaction revealed intriguing reactivity nucleophilic time. second with use allenylethylene carbonates π-oxyallyl-Pd precursors, presented unique under different conditions provide divergent synthetic access (E)- (Z)-allenyl diene products. Interestingly, subsequent sequential intramolecular cyclization/isomerization (Z)-product delivered dihydrooxepine derivatives [5 + 2] annulation
Язык: Английский
Процитировано
10
Chemical Communications, Год журнала: 2024, Номер 60(11), С. 1436 - 1439
Опубликована: Янв. 1, 2024
Benzo-fused cyclic carbonates were designed and synthesized as a novel type of precursor π-allylpalladium zwitterionic intermediates.
Язык: Английский
Процитировано
8
Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1680 - 1685
Опубликована: Янв. 1, 2023
An efficient approach for the exclusively regioselective construction of 1,5-di/ox-azonanes via Pd-catalyzed [5 + 4] cycloaddition has been developed.
Язык: Английский
Процитировано
14
Organic Letters, Год журнала: 2023, Номер 25(34), С. 6328 - 6333
Опубликована: Авг. 23, 2023
The 5-allenyloxazolidine-2,4-diones had been synthesized as novel precursors of π-allyl palladium zwitterion and were applied in a palladium-catalyzed enantioselective (3 + 2) annulation by using barbiturate-derived alkenes the reaction partner presence an axially chiral phosphoramidite ligand. This proceeded smoothly under mild conditions, affording highly functionalized spirobarbiturate-γ-lactam derivatives excellent yields along with high diastereo- enantioselectivities. scale-up further transformation product also successful.
Язык: Английский
Процитировано
12
Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(22), С. 3967 - 3972
Опубликована: Окт. 18, 2022
Abstract In this paper, we designed and synthesized 4‐vinyl‐4‐butyrolactone as a precursor to generate the zwitterionic allylpalladium intermediates, which behaved five‐membered all‐carbon synthon in palladium‐catalyzed (5+3) annulation with azomethine imines, giving eight‐membered ring‐fused heterocycles (26 examples, 49% 97% yield, >20:1 dr). magnified image
Язык: Английский
Процитировано
19
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Май 27, 2025
Considerable progress has been made over decades in synthetic organic chemistry order to build up molecular complexity, often through the design of advanced catalytic systems. Yet, simply exposing molecules benchmark oxidants catalyst free conditions can sometimes lead surprising and highly valuable products. Thus, a method for accessing rare 9-membered ketolactams is herein described, under mild oxidative conditions. Key 18O 17O label experiments revealed an unexpected oxygen atom migration event ring expansion process. The scope, mechanism, applications, 9 7 membered contraction opportunities are discussed.
Язык: Английский
Процитировано
0
Chemical Communications, Год журнала: 2022, Номер 58(75), С. 10560 - 10563
Опубликована: Янв. 1, 2022
A new approach for the synthesis of 9-membered N,N,O-heterocycles by Pd-catalyzed [6+3] dipolar cycloaddition N-iminoisoquinolinium ylides and 2-vinyl oxetanes has been developed. The scope this was demonstrated with 28 examples. This is another important synthetic strategy medium-sized rings employing as ternary synthons.
Язык: Английский
Процитировано
14
Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(5), С. 1299 - 1304
Опубликована: Дек. 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.
Язык: Английский
Процитировано
8