Catalytic Atroposelective Synthesis of N–N Axially Chiral Indolylamides DOI Creative Commons

Tian‐Zhen Li,

Shufang Wu,

Ning‐Yi Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12559 - 12575

Опубликована: Авг. 27, 2024

The catalytic atroposelective synthesis of N–N axially chiral indolylamides was established via dynamic kinetic resolution, which makes use Lewis base-catalyzed asymmetric acylation N-acylaminoindoles as a new type platform molecule with anhydrides. By this strategy, series were synthesized in overall good yields (up to 98%) excellent enantioselectivities 99% ee). Moreover, some these display extent anticancer activity, demonstrates their potential application medicinal chemistry. Therefore, work has not only provided strategy for the monoaryl indoles but also offered member configurational stability and promising application, thereby solving challenges indoles.

Язык: Английский

NHC-Catalyzed Chemo- and Enantioselective Reaction between Aldehydes and Enals for Access to Axially Chiral Arylaldehydes DOI
Zhiguo Zheng, Qian Liu,

Xiaolin Peng

и другие.

Organic Letters, Год журнала: 2024, Номер 26(4), С. 917 - 921

Опубликована: Янв. 18, 2024

A chiral carbene-catalyzed chemo- and enantioselective reaction with racemic biaryl aldehydes α-bromoenals is developed for access to axially 2-arylbenzaldehydes through atroposelective dynamic kinetic resolution (DKR) processes. This DKR strategy can tolerate a broad scope of substrates diverse functionalities. The 2-aryl benzaldehyde products generally afford moderate good yields enantioselectivities. molecules afforded from the current approach are variable simple transformations functional excellent optical purities.

Язык: Английский

Процитировано

5

Axially Chiral Bridged Biaryls by Ni-Catalyzed Kinetic Asymmetric C–O Bond Cleavage DOI
Yijun Fang,

Jiameng Hu,

Tingting Sun

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(11), С. 8176 - 8183

Опубликована: Май 10, 2024

Axially chiral bridged biaryls represent an important subset of axially biaryl scaffolds in fields ranging from organic synthesis to biochemistry materials science. While numerous catalytic strategies have been elucidated for the construction axial chirality, enantioenriched form remains underdeveloped. Herein, we demonstrate approach synthesize diverse through nickel-catalyzed kinetic asymmetric cleavage unactivated aromatic C–O bond. The system features mild reaction conditions, high resolution efficiency, and versatile post-functionalizations. Mechanistic studies reveal impact nickel catalyst's chirality on stereochemical output this transformation.

Язык: Английский

Процитировано

4

Catalytic Atroposelective Construction of Furan‐Based Axially Chiral Scaffolds DOI

Wei Tan,

Xinyue Wu, Feng Shi

и другие.

ChemCatChem, Год журнала: 2024, Номер 16(21)

Опубликована: Июль 19, 2024

Abstract Axially chiral furan‐based scaffolds have been recognized as a class of important five‐membered heteroaryl atropisomers, and developing catalytic atroposelective reactions for constructing this is highly desirable. However, the construction such rather underdeveloped due to existence great challenges remote ortho ‐substituents weak configurational stability. To overcome these challenges, synthetic chemists recently paid attention research field, number axially constructed via using different strategies. This concept summarized advances in field pointed out remaining which will promote further development emerging field.

Язык: Английский

Процитировано

4

Organocatalytic diastereo- and atropo-selective construction of eight-membered bridged (hetero)biaryls via asymmetric intramolecular [3 + 2] cycloaddition DOI Creative Commons

Yue Wang,

Yue Huang, Xiaoze Bao

и другие.

Chemical Science, Год журнала: 2024, Номер 15(23), С. 8880 - 8887

Опубликована: Янв. 1, 2024

Axially chiral eight-membered bridged (hetero)biaryls have been constructed via organocatalytic intramolecular [3 + 2] cycloaddition of innovative (hetero)biaryl aldehydes with 3-amino oxindole hydrochlorides.

Язык: Английский

Процитировано

3

Catalytic Atroposelective Synthesis of N–N Axially Chiral Indolylamides DOI Creative Commons

Tian‐Zhen Li,

Shufang Wu,

Ning‐Yi Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12559 - 12575

Опубликована: Авг. 27, 2024

The catalytic atroposelective synthesis of N–N axially chiral indolylamides was established via dynamic kinetic resolution, which makes use Lewis base-catalyzed asymmetric acylation N-acylaminoindoles as a new type platform molecule with anhydrides. By this strategy, series were synthesized in overall good yields (up to 98%) excellent enantioselectivities 99% ee). Moreover, some these display extent anticancer activity, demonstrates their potential application medicinal chemistry. Therefore, work has not only provided strategy for the monoaryl indoles but also offered member configurational stability and promising application, thereby solving challenges indoles.

Язык: Английский

Процитировано

3