Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2554 - 2560
Published: Jan. 1, 2024
A three-component one-pot reaction of TMSCF 2 Br, p -QMs and 1,3-dicarbonyl compounds derivatives was developed. series densely functionalized tetra-substituted furans pyrroles were constructed with excellent chemoselectivities.
Language: Английский
The Chemical Record, Journal Year: 2021, Volume and Issue: 21(12), P. 4150 - 4173
Published: Aug. 9, 2021
In the last few years, there has been an explosive growth in area of para-quinone methide (p-QM) chemistry. This boom is actually due to unique reactivity pattern p-QMs, and also their remarkable synthetic applications. fact, p-QMs serve as synthons for unsymmetrical diaryl- triarylmethanes, construction diverse range carbocycles heterocycles. a wide structurally complex heterocyclic frameworks could be accessed through transformations modified stable p-QMs. Therefore, main focus this review article cover recent advancements transition-metal, Lewis acid base-catalyzed/mediated p-quinone methides (p-QMs) oxygen- nitrogen-containing
Language: Английский
Citations
65
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3657 - 3665
Published: Feb. 17, 2024
A practical and regioselective direct N-alkylation of 2-pyridones is enabled by use α-keto esters in the P(NMe2)3-mediated deoxygenation process. The reaction proceeds under mild conditions to produce N-alkylated with high selectivity generality, protocol shown be applicable for scale-up synthesis, which makes it promising applications.
Language: Английский
Citations
6
Tetrahedron, Journal Year: 2023, Volume and Issue: 148, P. 133655 - 133655
Published: Oct. 9, 2023
Language: Английский
Citations
14
The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(8), P. 5213 - 5228
Published: April 4, 2022
The addition of α-ketoamide to p-quinone methide initiated by dialkylphosphite in the presence organic base 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) is explored. Coupling dialkylphosphites α-ketoamides a follows [1,2]-phospha-Brook rearrangement, generating corresponding α-phosphonyloxy enolates that are subsequently seized methides (p-QMs). two-step one-pot 1,6-conjugate provides effective access series isatin-incorporated phosphate-bearing 1,6-adducts having two vicinal tertiary carbons with up 90% yield and >20:1 dr.
Language: Английский
Citations
18
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 9987 - 10001
Published: July 5, 2023
A facile one-pot metal-free, base-mediated formal [3 + 2] and [4 dearomative ipso-cycloaddition of para-quinone methides (p-QMs) with halo alcohols has been designed for the efficient construction 2-oxa-spirocyclohexadienones in excellent yield under mild reaction conditions. The commercial availability bases, reagents, convenient procedure makes it an attractive method ipso-cyclization.
Language: Английский
Citations
10
Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7595 - 7600
Published: Oct. 13, 2023
O-Phosphination of α-dicarbonyls via sequential in situ formation a Kukhtin-Ramirez adduct and P(NMe2)3-catalyzed process has been exploited for the synthesis α-phosphoryloxy carbonyls. A range P(O)-H derivatives, including diarylphosphine oxides, arylphosphinates, phosphinates, are competent candidates to be introduced into this transformation, various carbonyls obtained. This approach possesses advantages mild conditions, simple operations, atom economy, high efficiency, gram-scale synthesis, which make it promising toolbox.
Language: Английский
Citations
10
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6100 - 6105
Published: April 15, 2024
Fluorooxindoles undergo asymmetric Michael addition to para-quinone methides under phase-transfer conditions with 10 mol% of a readily available cinchona alkaloid ammonium catalyst. This reaction affords sterically encumbered, multifunctional fluorinated organic compounds displaying two adjacent chirality centers high yields, ee's and dr's.
Language: Английский
Citations
3
Organic Letters, Journal Year: 2021, Volume and Issue: 23(15), P. 5885 - 5890
Published: July 19, 2021
A new tandem annulation of p-quinone methides (p-QMs) with ynamides is described. This cascade reaction features a unique combination (2 + 2) annulation, retro-4π electrocyclization, and imino-Nazarov cyclization, wherein vinyl (p-VQMs) as one the key intermediates have been identified chemically. Significantly, an unusual structural reconstruction p-QMs involving cleavage C5–C6 bond late-stage formation C4–C6 involved, leading to methodology development for construction functionalized aminoindenes.
Language: Английский
Citations
23
Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(7), P. 1496 - 1502
Published: Jan. 1, 2021
A
new
copper-catalyzed
radical-triggered
fluoromethylation-spirotricyclization
of
enediyne-
and
enyne-nitrile-containing
Language: Английский
Citations
21
The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(11), P. 7490 - 7499
Published: May 18, 2021
A novel Brønsted acid catalyzed 1,8-addition mediated (3 + 4)-annulation of in situ generated propargylic p-quinone methides with 2-indolylmethanols is described. This method provides a convenient and mild approach to structurally interesting synthetically important polysubstituted indole-fused oxepines high yields. Moreover, as four-atom synthons the 4)-annulations under conditions have been explored for first time.
Language: Английский
Citations
21