Brønsted-Acid-Catalyzed Enantioselective Desymmetrization of 1,3-Diols: Access to Chiral β-Amino Alcohol Derivatives DOI

Da-Qiu Cui,

Yuqi Wang, Bo Zhou

и другие.

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

Construction of Axially Chiral Arylpyrroles via Atroposelective Diyne Cyclization DOI

Yang‐Bo Chen,

Li‐Gao Liu,

Can‐Ming Chen

и другие.

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

Isoxazoles as efficient alkyne amination reagents in divergent heterocycle synthesis DOI Creative Commons
Xiao-Kang Zhu, Zhe Meng, Bo Zhou

и другие.

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

Organocatalytic intramolecular (4 + 2) annulation of enals with ynamides: atroposelective synthesis of axially chiral 7-aryl indolines DOI Creative Commons
Zhixin Zhang, Li‐Gao Liu, Yixi Liu

и другие.

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

Synthesis of functionalized sulfilimines via iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds DOI

Xianda Wu,

Minghong Chen, Fu‐Sheng He

и другие.

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

Copper-catalyzed enantioselective desymmetrizing C(sp2)–H functionalization of azide-ynamides via α-imino copper carbenes DOI

En‐He Huang,

Li‐Gao Liu,

Yin You-wei

и другие.

Science China Chemistry, Год журнала: 2024, Номер 67(9), С. 2982 - 2988

Опубликована: Июль 3, 2024

Язык: Английский

Процитировано

4

Copper-Catalyzed Tandem Cyclization/Direct C(sp2)–H Annulation of Azide–Ynamides via α-Imino Copper Carbenes: Access to Azepino[2,3-b:4,5-b′]diindoles DOI
Yi Chen,

Yao-Hong Yan,

Bo‐Han Zhu

и другие.

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

Catalytic Asymmetric Rearrangement of Azoalkene-Derived Sulfonium Ylides via Remote Chirality Control DOI
Kaixuan Wang,

Zhiqian Yu,

Zheng Tan

и другие.

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

Copper-Catalyzed Formal [4 + 1] Annulation of Diynes with Isoxazoles: Synthesis of Pyrrolo[3,4-b]indoles DOI

Tian-Qi Hu,

Ya-Nan Meng,

Yijie Zheng

и другие.

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

Enantioselective Desymmetrizing Hydroalkoxylation of 1,4- and 1,8-Diynes Enabled by Chiral Brønsted Acid Catalysis DOI
Yin Xu,

Gan-Lu Qian,

Da-Qiu Cui

и другие.

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

Gold‐Catalyzed Cyclization of Yndiamides with Isoxazoles via α‐Imino Gold Fischer Carbenes DOI Creative Commons

Zixuan Tong,

Philip Cameron‐Smith, Helena D. Pickford

и другие.

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