Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates DOI Open Access
Qian Liu,

Kunpeng Teng,

Yi Zhang

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(46)

Опубликована: Июль 25, 2024

Abstract An unprecedented chemodivergent strategy for parallel kinetic resolution (PKR) is disclosed through which two planar chiral products bearing different structures were simultaneously afforded with opposite stereoselectivities. Two achiral esters are activated by one single N‐heterocyclic carbene (NHC) catalyst to react the enantiomers of racemic imine substrate in a fashion. distinct and stereoselectivities respectively from same reaction system good excellent yields, enantio‐ diastereoselectivities. Control experiments studies carried out probe dynamic properties during progress. The pyridine lactam show interesting applications both asymmetric synthesis pesticide development.

Язык: Английский

Catalyst-Controlled Switchable (5 + 4)/(3 + 4) Cycloadditions for the Divergent Synthesis of Pyrazole-Fused Seven- and Nine-Membered Heterocycles DOI
Jie Wang, Ting Qi,

Shurong He

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(16), С. 10694 - 10704

Опубликована: Авг. 1, 2023

Developing diversity-oriented synthetic approaches for medium-sized rings is of great interest, and the divergent synthesis with different ring sizes poses a challenging task. In this study, we present catalyst-controlled switchable (5 + 4)/(3 4) cycloaddition strategy seven- nine-membered heterocycles. Utilizing two 4-aminopyridine Lewis base catalysts, pyrazole-fused benzazepines or benzoxazonines can be efficiently assembled from same substrates. These products exhibit good stability without interconversion under reaction conditions elevated temperatures. The origin chemoselectivity was elucidated by means computational studies involving DFT calculations, distortion/interaction analysis, noncovalent interaction analysis.

Язык: Английский

Процитировано

16

Chemodivergent Parallel Kinetic Resolution of Paracyclophanes: Enantiomer Fishing with Different Substrates DOI
Qian Liu,

Kunpeng Teng,

Yi Zhang

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(46)

Опубликована: Июль 25, 2024

Abstract An unprecedented chemodivergent strategy for parallel kinetic resolution (PKR) is disclosed through which two planar chiral products bearing different structures were simultaneously afforded with opposite stereoselectivities. Two achiral esters are activated by one single N‐heterocyclic carbene (NHC) catalyst to react the enantiomers of racemic imine substrate in a fashion. distinct and stereoselectivities respectively from same reaction system good excellent yields, enantio‐ diastereoselectivities. Control experiments studies carried out probe dynamic properties during progress. The pyridine lactam show interesting applications both asymmetric synthesis pesticide development.

Язык: Английский

Процитировано

6

1,3-Indanedione: An versatile building block DOI Creative Commons
Chao‐Guo Yan

Green Synthesis and Catalysis, Год журнала: 2022, Номер 4(2), С. 78 - 88

Опубликована: Дек. 14, 2022

Indanone-containing compounds are very important components of various natural products, chemical drugs, agrochemicals and functionalized material fields. 1,3-Indanedione is a typical cyclic 1,3-dicarbonyl compound with three contiguous reactive electrophilic nucleophilic sites. The easily prepared 2-arylidene-1,3-indanediones active α,β-unsaturated carbonyl could act as 1,3-dipolarophile, 1,4-dienophile 1-oxa-1,3-diene, etc. On the other hand, homodimer (bindone) cyclotrimer (truxenone) derived from base-catalyzed self-condensation 1,3-indanedione also compounds. Therefore, its derivatives can be employed key substrates in domino multicomponent reactions. In this review, we summarized recent progress on reactions 1,3-indanedione, especially our achievements synthetic applications for complex indanone-containing carbocyclic heterocyclic

Язык: Английский

Процитировано

13

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

DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons DOI

Jiaxin Qu,

Thomas P. Yang, Xin Zhao

и другие.

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9322 - 9327

Опубликована: Окт. 24, 2024

The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction epoxides, simultaneously providing rare oxygen-containing active intermediate in this field. gram-scale preparation and facile derivatization cycloadduct highlight significant synthetic potential strategy.

Язык: Английский

Процитировано

2

Organocatalytic (5+1) benzannulation of Morita–Baylis–Hillman carbonates: synthesis of multisubstituted 4-benzylidene pyrazolones DOI

Shurong He,

Jie Wang,

Jinfeng Zheng

и другие.

New Journal of Chemistry, Год журнала: 2022, Номер 46(24), С. 11617 - 11622

Опубликована: Янв. 1, 2022

DABCO-catalyzed (5+1) cycloaddition of MBH carbonate undergoes an α-double deprotonation pathway to de novo assemble the benzene ring.

Язык: Английский

Процитировано

10

DMAP-Catalyzed [4+3] Spiroannulation of Pyrazolone-Derived Morita–Baylis–Hillman Carbonates with N-(o-Chloromethyl)aryl Amides to Forge Spiro[pyrazolone-azepine] Scaffolds DOI

Xingfu Wei,

Yue Huang,

Zahra Karimi

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 10190 - 10198

Опубликована: Июнь 30, 2023

A novel DMAP-catalyzed [4+3] spiroannulation of pyrazolone-derived Morita-Baylis-Hillman carbonates with N-(o-chloromethyl)aryl amides was developed. This reaction led to the assembly medicinally relevant pyrazolone and azepine nuclei into a structurally new spirocyclic scaffold, diverse array spiro[pyrazolone-azepine] products were afforded in good excellent yields (up 93%) wide substrate scope (23 examples) under mild conditions. Moreover, gram-scale product transformations conducted, which further increased diversity products.

Язык: Английский

Процитировано

5

Synthesis of functionalized spiro[indanone-benzazepine] scaffolds via [4 + 3] annulation reaction of N-(o-chloromethyl)aryl amides with ninhydrin-derived Morita−Baylis−Hillman carbonates DOI Open Access
Kai‐Kai Wang, Junwei Ye,

Jun Jia

и другие.

Tetrahedron, Год журнала: 2023, Номер 150, С. 133772 - 133772

Опубликована: Дек. 1, 2023

Язык: Английский

Процитировано

5

Asymmetric [3+2] spiroannulation of pyrazolone-derived Morita–Baylis–Hillman carbonates with alkynyl ketones: facile access to spiro[cyclopentadiene-pyrazolone] scaffolds DOI

Xingfu Wei,

Yue Huang, Wenyao Wang

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(68), С. 9504 - 9507

Опубликована: Янв. 1, 2022

An organocatalyzed asymmetric [3+2] spiroannulation reaction of pyrazolone-derived MBH carbonates with alkynyl ketones was described, affording chiral spiro[cyclopentadiene-pyrazolone] scaffolds in good yields high degrees enantiocontrol.

Язык: Английский

Процитировано

7

Phosphine‐Catalyzed Domino Annulation Reactions of o‐Aminotrifluoroacetophenone Derivatives with Morita–Baylis–Hillman Carbonates: Construction of Tetrahydrofuro[3,2‐b]indolines DOI
Yannan Zhu, He Zhao,

Qiuyun Li

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2252 - 2256

Опубликована: Апрель 5, 2024

Abstract The domino annulation reactions of o ‐aminotrifluoroacetophenone derivatives and MBH carbonates enabled by PPh 3 have been reported, which provide a series tetrahydrofuro[3,2‐b]indolines containing CF ‐substituted tetrasubstituted carbon stereocenters in yields 74 to 95% >20:1 dr. In this process, were used as C1/C3 synthons. MTT assay shows that the products exhibit activity inhibitory effect on proliferation Hela cancer cell line.

Язык: Английский

Процитировано

1