Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 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.
Language: Английский
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(13), P. 9940 - 9954
Published: June 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
Language: Английский
Citations
9
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(11), P. 1436 - 1439
Published: Jan. 1, 2024
Benzo-fused cyclic carbonates were designed and synthesized as a novel type of precursor π-allylpalladium zwitterionic intermediates.
Language: Английский
Citations
8
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 18, 2024
A Pd-catalyzed asymmetric higher-order dipolar cycloaddition between allenyl carbonates and azadienes is achieved by exploiting novel alkylidene-π-allyl-Pd dipoles. This research provides a modular platform for the synthesis of challenging chiral endocyclic allenes bearing medium-sized heterocyclic motif centrally stereocenter in good yields with high enantio- diastereoselectivities (29 examples, up to 97% yield, 97:3 er >19:1 dr). Experimental computational studies elucidate possible reaction mechanism observed stereochemical results. Based on mechanistic understanding, new π-propargyl-Pd dipole was designed further extend success higher order strategy 10-membered alkynes from propargyl (13 98% yield 94.5:5.5 er).
Language: Английский
Citations
8
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5019 - 5028
Published: March 19, 2024
In this paper, we reported the palladium-catalyzed formal [5 + 4] cycloaddition reactions between 4-vinyl-4-butyrolactones (VBLs) and azadienes. Under mild reaction conditions, a wide range of benzofuran-fused 9-membered heterocyclic compounds had been provided in moderate to excellent yields with exclusive regioselectivities diastereoselectivities. The practical applicability synthesis was demonstrated through scale-up further transformation.
Language: Английский
Citations
5
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 10, 2025
A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as reagents has been developed. Under the catalysis Pd(PPh3)4, a wide range γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild conditions, broad substrate scope, functional group tolerance, suitable for gram-scale synthesis.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 960 - 965
Published: Jan. 19, 2024
Divergent transformations of allenylethylene carbonates with diboron reagents catalyzed by copper are disclosed. By using CuCl/IPr·HCl as the catalyst, react B2hex2 to afford 2,4-dien-1-ols product in presence Cs2CO3 base, iPrOH additive, and 1,4-dioxane solvent. And they B2pin2 form boronic half acids NaOtBu water THF The reactions corresponding products good stereoselectivities yields, further derivatizations study mechanism also demonstrated.
Language: Английский
Citations
3
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(24)
Published: Feb. 21, 2024
In this paper, Pd-catalyzed [4+2] decarboxylative cycloaddition of 4-vinylbenzodioxinones with barbiturate-derived alkenes has been developed, leading to various spirobarbiturate-chromane derivatives in high yields excellent diastereo- and enantioselectivities. The scale-up reaction further derivation the product were demonstrated. A plausible mechanism was also proposed.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8951 - 8959
Published: May 30, 2024
Palladium-catalyzed (4 + 1) annulation of 4-vinylbenzodioxinones with sulfur ylides has been developed to afford various dihydrobenzofuran derivatives in moderate high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating application potential current organic synthesis.
Language: Английский
Citations
1
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
Citations
1
Chemical Science, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 26, 2024
The first Ni-catalyzed asymmetric decarboxylative strategy for the construction of carbocycles with contiguous quaternary all-carbon stereocenters is reported. key to success these reactions utilization rationally designed allenylic methylene cyclic carbonates as substrates Ni catalysis. floppy group exerts unique electronic properties on carbonate, which allows further nucleophilic annulations alkenes. These can be performed at room temperature and feature wide functional tolerance excellent induction that typically >94% ee. mechanistic insights imply this conceptually new chemistry completely different from previous reports catalytic transformation carbonates, thus, it offers an inventive novel methodology create complex enantio-enriched molecules.
Language: Английский
Citations
1