Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2554 - 2560
Опубликована: Янв. 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.
Язык: Английский
The Chemical Record, Год журнала: 2021, Номер 21(12), С. 4150 - 4173
Опубликована: Авг. 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
Язык: Английский
Процитировано
66
Tetrahedron, Год журнала: 2023, Номер 148, С. 133655 - 133655
Опубликована: Окт. 9, 2023
Язык: Английский
Процитировано
15
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3657 - 3665
Опубликована: Фев. 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.
Язык: Английский
Процитировано
6
The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(8), С. 5213 - 5228
Опубликована: Апрель 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.
Язык: Английский
Процитировано
18
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 9987 - 10001
Опубликована: Июль 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.
Язык: Английский
Процитировано
10
Organic Letters, Год журнала: 2023, Номер 25(42), С. 7595 - 7600
Опубликована: Окт. 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.
Язык: Английский
Процитировано
10
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6100 - 6105
Опубликована: Апрель 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.
Язык: Английский
Процитировано
4
Organic Letters, Год журнала: 2021, Номер 23(15), С. 5885 - 5890
Опубликована: Июль 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.
Язык: Английский
Процитировано
23
Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(7), С. 1496 - 1502
Опубликована: Янв. 1, 2021
A
new
copper-catalyzed
radical-triggered
fluoromethylation-spirotricyclization
of
enediyne-
and
enyne-nitrile-containing
Язык: Английский
Процитировано
21
The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(11), С. 7490 - 7499
Опубликована: Май 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.
Язык: Английский
Процитировано
21