Advances in Atroposelectively De Novo Synthesis of Axially Chiral Heterobiaryl Scaffolds DOI Creative Commons
Xiaoke Zhang, Yazhou Liu, Huawu Shao

и другие.

Molecules, Год журнала: 2022, Номер 27(23), С. 8517 - 8517

Опубликована: Дек. 3, 2022

Axially chiral heterobiaryl frameworks are privileged structures in many natural products, pharmaceutically active molecules, and ligands. Therefore, a variety of approaches for constructing these skeletons have been developed. Among them, de novo synthesis, due to its highly convergent superior atom economy, serves as promising strategy access challenging scaffolds including C-N, C-C, N-N axes. So far, several elegant reviews on the synthesis axially disclosed, however, atroposelective construction subunits by was rarely covered. Herein, we summarized recent advances catalytic asymmetric scaffold via synthetic strategies. The related mechanism, scope, applications were also included.

Язык: Английский

Catalytic Generation of Remote C–N Axial Chirality through Atroposelectivede novoArene Construction DOI
Subhajit Mondal, Santanu Mukherjee

Organic Letters, Год журнала: 2022, Номер 24(45), С. 8300 - 8304

Опубликована: Ноя. 4, 2022

The first atroposelective desymmetrization of prochiral N-aryl maleimides through its conversion to axially chiral phthalimides is developed by applying a de novo arene construction strategy. Catalyzed bis(3,5-dimethylphenyl)prolinol TMS-ether, this reaction proceeds oxidative [4 + 2]-cycloaddition with α,β-unsaturated aldehydes generate only C-N axis remote from the sites excellent enantioselectivity (up 97.5:2.5 er).

Язык: Английский

Процитировано

14
Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors DOI Creative Commons
Jing Jiang, Jin Zhou, Yang Li

и другие.

Communications Chemistry, Год журнала: 2023, Номер 6(1)

Опубликована: Июнь 19, 2023

Significant progress has been made in asymmetric synthesis through the use of transition metal catalysts combined with Lewis bases. However, a dual catalytic system involving 4-aminopyridine and received little attention. Here we show metal/Lewis base relay featuring silver acetate modified chiral pyrrolidinopyridine (PPY). It was successfully applied cycloisomerization/(2 + 3) cycloaddition reaction enynamides. Bispirocyclopentene pyrazolone products could be efficiently synthesized stereoselective economical manner (up to >19:1 dr, 99.5:0.5 er). Transformations product access stereodivergent diastereoisomers densely functionalized polycyclic derivatives. Mechanistic studies illustrated model origin uncommon chemoselectivity. In subsequent bioassays, containing privileged drug-like scaffold exhibited isoform-selective phosphodiesterase 1 (PDE1) inhibitory activity vitro. The optimal lead compound displayed good therapeutic effect for ameliorating pulmonary fibrosis via inhibiting PDE1 vivo.

Язык: Английский

Процитировано

8
Nitro-Enabled Atroposelective Dynamic Kinetic Resolution of 2-Arylindoles by Phase-Transfer Catalysis DOI
Chanhee Lee, Su Jin Lee, Ahreum Kim

и другие.

Organic Letters, Год журнала: 2024, Номер 26(3), С. 681 - 686

Опубликована: Янв. 17, 2024

This study presents the atroposelective alkylation of 2-arylindoles catalyzed by a substituted cinchonium salt as phase-transfer catalyst. Under optimized reaction conditions, various substrates are employed to yield products with high enantioselectivity. The presence an ortho-nitro group at aromatic ring is essential for atroposelectivity, because it facilitates favorable interactions between catalyst and substrate. origin enantioselectivity reveals π–π both enantiomers unfavorable steric strains undesired enantiomers.

Язык: Английский

Процитировано

2
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

2
Advances in Atroposelectively De Novo Synthesis of Axially Chiral Heterobiaryl Scaffolds DOI Creative Commons
Xiaoke Zhang, Yazhou Liu, Huawu Shao

и другие.

Molecules, Год журнала: 2022, Номер 27(23), С. 8517 - 8517

Опубликована: Дек. 3, 2022

Axially chiral heterobiaryl frameworks are privileged structures in many natural products, pharmaceutically active molecules, and ligands. Therefore, a variety of approaches for constructing these skeletons have been developed. Among them, de novo synthesis, due to its highly convergent superior atom economy, serves as promising strategy access challenging scaffolds including C-N, C-C, N-N axes. So far, several elegant reviews on the synthesis axially disclosed, however, atroposelective construction subunits by was rarely covered. Herein, we summarized recent advances catalytic asymmetric scaffold via synthetic strategies. The related mechanism, scope, applications were also included.

Язык: Английский

Процитировано

10