Organic Letters, Год журнала: 2023, Номер 25(51), С. 9130 - 9135
Опубликована: Дек. 19, 2023
Herein, we describe a Brønsted-acid-catalyzed enantioselective desymmetrization of 1,3-diols with alkynes through hydroalkoxylation/hydrolysis process. The reaction leads to the atom-economical synthesis valuable chiral β-amino alcohols under mild conditions. Further synthetic transformations based on alcohol moiety provide divergent approaches toward N-containing heterocycles.
Язык: Английский
Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(23)
Опубликована: Март 30, 2023
Axially chiral biaryls widely exist in natural products and pharmaceuticals are used as ligands catalysts asymmetric synthesis. Compared to the well-established axially 6-membered biaryl skeletons, examples of 5-membered have been quite scarce, mono-substituted 3-arylpyrrole atropisomers not reported. Here, we disclose a copper-catalyzed atroposelective diyne cyclization for construction range arylpyrrole good excellent yields with generally enantioselectivities via oxidation X-H insertion vinyl cations. Importantly, this protocol only represents first synthesis atropisomers, but also constitutes example atropisomer Theoretical calculations further support mechanism cation-involved elucidate origin enantioselectivity.
Язык: Английский
Процитировано
34
Chemical Society Reviews, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
This review summarizes the latest trends and developments of isoxazole-enabled alkyne amination reactions their applications in divergent heterocycle synthesis.
Язык: Английский
Процитировано
2
Chemical Science, Год журнала: 2023, Номер 14(22), С. 5918 - 5924
Опубликована: Янв. 1, 2023
Catalytic enantioselective transformation of alkynes has become a powerful tool for the synthesis axially chiral molecules. Most these atroposelective reactions rely on transition-metal catalysis, and organocatalytic approaches are largely limited to special which act as precursors Michael acceptors. Herein, we disclose an intramolecular (4 + 2) annulation enals with ynamides. This method allows efficient highly atom-economical preparation various 7-aryl indolines in generally moderate good yields excellent enantioselectivities. Computational studies were carried out elucidate origins regioselectivity enantioselectivity. Furthermore, phosphine ligand derived from synthesized indoline was proven be potentially applicable asymmetric catalysis.
Язык: Английский
Процитировано
12
Green Chemistry, Год журнала: 2023, Номер 25(22), С. 9092 - 9096
Опубликована: Янв. 1, 2023
An efficient iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds for the synthesis functionalized sulfilimines is developed under air conditions.
Язык: Английский
Процитировано
12
Science China Chemistry, Год журнала: 2024, Номер 67(9), С. 2982 - 2988
Опубликована: Июль 3, 2024
Язык: Английский
Процитировано
4
Organic Letters, Год журнала: 2023, Номер 25(12), С. 2063 - 2067
Опубликована: Март 20, 2023
A novel copper-catalyzed tandem cyclization/direct C(sp2)–H annulation of phenyl azide–ynamides via α-imino copper carbenes has been developed, which provides a concise and flexible approach for the construction range valuable azepino[2,3-b:4,5-b′]diindoles in mostly good to excellent yields with high chemoselectivities. This reaction also exhibits broad substrate scope, functional group tolerance, simple operation, mild conditions.
Язык: Английский
Процитировано
9
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Март 26, 2025
The [2,3]-sigmatropic rearrangement has been widely utilized to construct C-S bonds. Herein, we report an enantioselective, intermolecular, and noncarbenoid of sulfonium ylides using azoalkenes. This process features a broad substrate scope, high efficiency, excellent enantioselectivity, achieving yields up 99% enantiomeric excess (ee) 96%. Furthermore, the protocol demonstrated good scalability.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Май 14, 2025
Catalytic annulation of isoxazoles with alkynes is an efficient methodology for the assembly N-heterocyclic architectures, and most reactions require noble-metal catalysts. Herein, we disclose a copper-catalyzed formal [4 + 1] 1,6-diynes atom-economical construction biologically important pyrrolo[3,4-b]indoles in high yields via vinyl cation intermediates, which significantly different from previous annulations involving α-imino metal carbene intermediates. Interestingly, preliminary results have been obtained related catalytic atroposelective transformation. Computational mechanistic studies are employed to elucidate reaction mechanism.
Язык: Английский
Процитировано
0
ACS Catalysis, Год журнала: 2023, Номер 13(13), С. 8803 - 8812
Опубликована: Июнь 19, 2023
Herein, an organocatalytic enantioselective desymmetrizing hydroalkoxylation of 1,4- and 1,8-diynes is disclosed, which represents a unique chiral Brønsted acid-catalyzed desymmetrization diynes. This protocol provides facile practical access to enantioenriched 1,3-diaminopropanol derivatives γ-butyrolactones with wide substrate scope generally high enantioselectivities. Besides, the backbones these products constitute structural core numerous bioactive molecules, they can serve as valuable precursors for expeditious assembly versatile N- O-heterocycles. Moreover, control experiments theoretical calculations are employed confirm mechanistic rationale elucidate origin enantioinduction.
Язык: Английский
Процитировано
8
Chemistry - A European Journal, Год журнала: 2023, Номер 29(70)
Опубликована: Сен. 28, 2023
Abstract Gold catalysis is an important method for alkyne functionalization. Here we report the gold‐catalyzed formal [3+2] aminative cyclization of yndiamides and isoxazoles in a direct synthesis polysubstituted diaminopyrroles, which are motifs drug discovery. Key to this process formation, subsequent cyclization, α‐imino gold Fischer carbene, represents new type carbene intermediate. The reaction proceeds rapidly under mild conditions, with high regioselectivity being achieved by introducing subtle steric bias between nitrogen substituents on yndiamide. DFT calculations revealed that key was interconversion isomeric keteniminiun ions via low‐barrier π‐complex transition state, establishes Curtin‐Hammett scenario isoxazole addition. By using benzisoxazoles as substrates, outcome could be switched [5+2] leading 1,4‐oxazepines.
Язык: Английский
Процитировано
8