European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 28, 2024
Abstract An efficient method has been developed for the preparation of 1,4‐naphthoquinones via a palladium‐catalyzed reaction 2‐aryl‐1,3‐indandiones with olefins. This involves tertiary C−H alkylation olefins to produce alcohol, followed by C−C bond cleavage.
Language: Английский
Organic Letters, Journal Year: 2024, Volume and Issue: 26(19), P. 4111 - 4116
Published: May 8, 2024
By integration of oxocarbenium activation and Lewis acid coordination via conformational proximity-driven, Pd(II)- or Cu(I)-catalyzed intramolecular ketone haloacylation, regio- stereoselective heterolytic ring-opening 1,5-haloacylation cyclopropyl ketones, including those with weak single alkyl donors, has been developed for the synthesis valuable α-quaternary halo-γ-butenolides. The vicinal carboxylic acceptors are no longer just spectator activators. Further, this reaction delivers a constant regioselectivity regardless electronic nature substituents, even malonate.
Language: Английский
Citations
4
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 24, 2025
Tf2NH-mediated regio- and diastereoselective skeletal metamorphosis of 1-alkynyl-2,3-diaryl-2-methoxycarbonylcyclopropyl ketones readily gave 2,3,4,5-tetraaryl-2,3-dihydrofurans. Controllable reduction removal the ester group then precisely afforded four types eight possible tetrahydrofuran (THF) diastereomers with different (hetero)aryl substituents. Further, deuterium-labeling results revealed an unprecedented hydrogen transfer from formyl C-H bond in tBuOK-promoted decarbonylation under tBuOH-free conditions.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: April 7, 2025
Herein we describe the first transition-metal-catalyzed asymmetric Cloke-Wilson rearrangement through unprecedented propargylic alkenoxylation reaction with enol as O-nucleophile. A set of new chiral PPBOX ligands was prepared to guarantee high enantioselectivity transformation. series polysubstituted dihydrofuran skeletons bearing an alkyne unit in good yield and under very mild conditions, various downstream transformations were facilely conducted access different skeletons.
Language: Английский
Citations
0
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 21, 2024
In contrast to the locked fluxionality of norcaradienes fused by benzene, unexplored less aromatic heterole-fused norcaradienes, creatively generated intramolecular hydroarylation heteroaryl alkynylcyclopropanes, reserve a balancing that permits dearomative [1,5]-sigmatropic carbon shift akin reduced aromaticity heterole. This "walk" was confirmed isolation cycloheptatriene species derived from ring-expansion dearomatized alkynylated norcaradiene. A following ester-directed ring-opening rearomatization these gives products featuring migratory acylmethyls are competent for helicenation with neighboring (hetero) arenes via (formal) dehydrative alkenylation. Such reactivity will open up opportunity development controllable reactions norcaradienes.
Language: Английский
Citations
2
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5304 - 5313
Published: April 9, 2024
Most of the known rearrangement reactions donor–acceptor cyclopropanes (DACs) involve migration cationic carbon atom to anionic or heteroatoms in 1,3- 1,4-positions. In present work, we observed that spiro DACs based on 1,3-indanedione 1-indanone moiety undergo intramolecular 1,2-aroyl when treated with titanium(IV) chloride afford 1,4-naphthoquinones and α-naphthols readily. The take place through formation putative 1,3-dipolar intermediates, followed by cleavage aroyl group adjacent ring-expansion products.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 19, 2024
In sharp contrast to the intuitive modulation by electronic effect, [4 + 1] annulation reaction between α-substituted conjugated enones and ylides has been reliably controlled match of α-substituent ylide in steric hindrance, providing a straightforward efficient method for valuable 4-cyano, 4-alkynyl, 4-vinyl, 4-aryl 2,3-dihydrofurans.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8017 - 8022
Published: Sept. 16, 2024
An atom-economic and diazo-free strategy for the construction of novel pseudo anomeric C-1 alkenyl spirocyclopropyl sugars is described. Leveraging 1,2-migration pathway propargyl esters under gold(I) catalysis, easily available
Language: Английский
Citations
0
Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 21, 2024
Abstract In contrast to the locked fluxionality of norcaradienes fused by benzene, unexplored less aromatic heterole‐fused norcaradienes, creatively generated intramolecular hydroarylation heteroaryl alkynylcyclopropanes, reserve a balancing that permits dearomative [1,5]‐sigmatropic carbon shift akin reduced aromaticity heterole. This “walk” was confirmed isolation cycloheptatriene species derived from ring‐expansion dearomatized alkynylated norcaradiene. A following ester‐directed ring‐opening rearomatization these gives products featuring migratory acylmethyls are competent for helicenation with neighboring (hetero) arenes via (formal) dehydrative alkenylation. Such reactivity will open up opportunity development controllable reactions norcaradienes.
Language: Английский
Citations
0
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 28, 2024
Abstract An efficient method has been developed for the preparation of 1,4‐naphthoquinones via a palladium‐catalyzed reaction 2‐aryl‐1,3‐indandiones with olefins. This involves tertiary C−H alkylation olefins to produce alcohol, followed by C−C bond cleavage.
Language: Английский
Citations
0