Organic Chemistry Frontiers, Год журнала: 2024, Номер 12(4), С. 1144 - 1149
Опубликована: Дек. 14, 2024
A squaramide-catalyzed regio-/enantioselective sulfa-1,6-addition initiated highly enantio- and diastereoselective desymmetrization of 2,5-cyclohexadienone-tethered 3-cyano-4-styrylcoumarins has been disclosed.
Язык: Английский
Organic Letters, Год журнала: 2023, Номер 25(21), С. 3835 - 3840
Опубликована: Май 19, 2023
Herein, a highly chemoselective 1,2-addition of thiols with 2-isothiocyanatochalcones followed by an enantioselective intramolecular thia-Michael addition cascade has been established to construct enantioenriched [1,3]-benzothiazine derivatives for the first time. The cinchona-derived squaramide catalyst provides good excellent yield and enantioselectivity products broad substrate adaptability. Furthermore, this strategy extended diphenylphosphine oxide nucleophile access organophosphorus-substituted [1,3]-benzothazines. A scale-up reaction synthetic transformation have demonstrated viability protocol.
Язык: Английский
Процитировано
9
Molecules, Год журнала: 2025, Номер 30(10), С. 2154 - 2154
Опубликована: Май 14, 2025
Domino reactions are powerful tools for the straightforward synthesis of complex molecules with a particular emphasis on functionalized azacycles. We report contribution in this field, implemented via new thia-Michael/aldol sequence between readily accessible N-alkoxyacrylamides and α,β-unsaturated carbonyls, access to polysubstituted δ-lactams acceptable-to-good yields good selectivity. This method, initially developed two-component approach characterized by mildness its reaction conditions, was shown be compatible various thiophenol derivatives employ simple pre-thiasilylation step one-pot process. further extension monotype aza-Michael/thia-Michael/aldol establishes proof-of-concept that acrylamides can react as both 1,3-bis-nucleophiles 1,4-electrophiles single flask operation.
Язык: Английский
Процитировано
0
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(17), С. 2789 - 2817
Опубликована: Июль 6, 2023
Abstract Quaternary stereogenic centers are of great importance because their prevalence in a series bioactive natural products and pharmaceuticals. Although the catalytic asymmetric construction these highly congested poses formidable challenge, this field has been extensively explored past few decades, several elegant strategies, such as conjugate addition to β,β‐disubstituted nitroalkenes, have developed. The resultant β‐nitro quaternary stereocenters can be conveniently transformed into corresponding β‐amino commonly found compounds. This review summarizes recent advances all‐carbon or hetero‐carbon via metal‐catalyzed organocatalyzed focusing on scope, applications, mechanisms reactions.
Язык: Английский
Процитировано
7
European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(16)
Опубликована: Фев. 16, 2024
Abstract We describe herein the direct electrophilic γ‐trifluoromethylthiolation and γ‐methylthiolation of enals, via in situ formation corresponding silyl dienol ether. This one‐pot process is carried out under simple mild reaction conditions compatible with a variety functional groups.
Язык: Английский
Процитировано
2
RSC Advances, Год журнала: 2024, Номер 14(12), С. 7992 - 7998
Опубликована: Янв. 1, 2024
The efficacy of green solvents and neat conditions in organocatalysed reactions were investigated. results suggest cyclopentyl methyl ether could serve as alternatives, potentially enhancing the processes' sustainability.
Язык: Английский
Процитировано
1
Chemistry - A European Journal, Год журнала: 2023, Номер 29(42)
Опубликована: Май 15, 2023
A highly diastereoselective organocatalyzed domino vinylogous sulfa-Michael-aldol-cyclocondensation (VMAC) reaction has been developed using alkylidene Meldrum's acid as dienes highlighting two steps, an unprecedented sulfa-1,6-conjugate addition and a aldol triggering formal (4+2) cycloaddition. This work opens new route towards bio-relevant original tricyclic thiochroman derivatives.
Язык: Английский
Процитировано
3
Phosphorus, sulfur, and silicon and the related elements, Год журнала: 2023, Номер 198(12), С. 981 - 985
Опубликована: Авг. 2, 2023
AbstractA facile sulfonylation of activated alkenes employing sodium arylsulfinates in Brønsted acidic deep eutectic solvent at room temperature has been developed. The choline chloride/p-toluenesulfonic acid acts both the and as catalyst, affording desired γ-keto sulfones good yields. Easily accessible starting materials, functional group compatibility well simple recovery make this procedure environmentally benign.Keywords: Sulfa-Michael reactionγ-keto sulfonessodium arylsulfinatesactivated alkenesdeep AcknowledgmentsThe authors thank Guoping Lu from Nanjing University Science Technology for his work on synthetic route design compound analysis.Disclosure statementThe declared that they have no conflicts interest to work. We declare we do not any commercial or associative represents a conflict connection with submitted.Additional informationFundingThis project was financially supported by “333” High-level Talent Project Jiangsu Province, Changzhou Sci & Tech Program (CJ20220021).
Язык: Английский
Процитировано
2
International Journal of Molecular Sciences, Год журнала: 2024, Номер 25(17), С. 9201 - 9201
Опубликована: Авг. 24, 2024
A new eco-friendly method for the synthesis of mono- and multifunctional organosulfur compounds, based on process between ynals thiols, catalyzed by bulky N-heterocyclic carbene (NHC), was designed optimized. The proposed organocatalytic approach allows straightforward formation a broad range thioesters sulfenyl-substituted aldehydes in yields above 86%, mild metal-free conditions. In this study, thirty-six sulfur-based derivatives were obtained characterized spectroscopic methods.
Язык: Английский
Процитировано
0
Organic Chemistry Frontiers, Год журнала: 2024, Номер 12(4), С. 1144 - 1149
Опубликована: Дек. 14, 2024
A squaramide-catalyzed regio-/enantioselective sulfa-1,6-addition initiated highly enantio- and diastereoselective desymmetrization of 2,5-cyclohexadienone-tethered 3-cyano-4-styrylcoumarins has been disclosed.
Язык: Английский
Процитировано
0