Asymmetric Synthesis of Tricycle‐Fused Dispirooxindoles via Organocatalyzed Three‐Component Cascade Reactions of 2‐Pyrones and Trifluoroethylisatin Ketimines DOI
Jing Xue, Meng Wang, Qian Zhao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(22), P. 3888 - 3894

Published: Oct. 7, 2022

Abstract An asymmetric synthesis of a series tricycle‐fused dispirooxindoles frameworks assembled in different rings was disclosed via multicomponent cascade 1,3‐dipolar cycloadditions electron‐deficient 2‐pyrones and trifluoroethylisatin ketimines under the catalysis hydroquinine or (DHQD) 2 PHAL with 61→99% ee >19:1 dr. Meanwhile, these potentially biologically important fused pyrrolidinyl/tetrahydropyranone/pyrrolidinyl frame‐works bear eight contiguous stereocenters functionalized pharmacophores which could further transfer to linaer spirooxindoles bearing epoxyethyl moiety retentive enantioselectivity. magnified image

Language: Английский

Lewis-Base-Catalyzed Enantioselective Formal [4 + 2] Annulations of Morita–Baylis–Hillman Carbonates: Access to Tetrahydroquinolines Derivatives DOI

Yanlin He,

Wei Cai, You Huang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3347 - 3351

Published: May 10, 2023

The Lewis-base-catalyzed enantioselective formal [4 + 2] annulation reaction of o-acylamino-aryl MBH carbonates and electron-deficient olefins was developed. Tetrahydroquinolines with three sequential stereogenic centers containing a quaternary stereocenter were obtained in high yields good enantioselectivity.

Language: Английский

Citations

26
Cooperative photoactivation/Lewis base catalyzed [4 + 2] annulations of α-diazoketones andortho-amino MBH carbonates to access dihydroquinolinone frameworks DOI
Jin Zhou, Chen Chen, Qiwen Pang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1034 - 1041

Published: Jan. 1, 2023

A series of dihydroquinolinones have been synthesized via synergistic catalysis combining photolysis and Lewis base utilizing in situ generated ketenes ortho -amino MBH carbonates.

Language: Английский

Citations

14
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

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(16), P. 10694 - 10704

Published: Aug. 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.

Language: Английский

Citations

14
Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles DOI
Qing‐Feng Li, Jing Ma,

Junjia Meng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4412 - 4439

Published: Nov. 16, 2023

Abstract Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made past years. Among them, organocatalysis, particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient reliable method preparation valuable functionalized spirooxindoles. According to different kinds catalysts, we summarize classify three catalytic strategies; tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed phosphine‐catalyzed respectively. Through methods, potential spirooxindole skeletons owning various functional groups can be produced enrich small organic molecule library. In this review, describe a comprehensive updated advances cycloaddition reactions Meanwhile, related mechanism application annulation strategies product total synthesis will highlighted detail.

Language: Английский

Citations

14
Visible-light-mediated sequential Wolff rearrangement and Staudinger cycloaddition enabling the assembly of spiro-pyrazolone-β-lactams DOI
Jie Tang,

Zhen-Hui Yan,

Gu Zhan

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(16), P. 4341 - 4346

Published: Jan. 1, 2022

Visible-light-mediated sequential Wolff rearrangement and Staudinger cycloaddition for the assembly of valuable spiro-pyrazolone-β-lactams.

Language: Английский

Citations

22
Remote stereocontrol in the (4 + 2) cycloadditions of 1,7-zwitterions: Asymmetric synthesis of multifunctionalized tetrahydroquinoline derivatives DOI
Chen Chen, Jin Zhou, Jing Jiang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(1), P. 108295 - 108295

Published: March 5, 2023

Language: Английский

Citations

8
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

et al.

Communications Chemistry, Journal Year: 2023, Volume and Issue: 6(1)

Published: June 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.

Language: Английский

Citations

8
Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines DOI Creative Commons
Kai‐Kai Wang, Wenwen Zhou,

Jun Jia

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(19), P. 6761 - 6761

Published: Sept. 22, 2023

Substrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 annulations between ninhydrin-derived Morita-Baylis-Hillman (MBH) adducts 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The provides a series novel structurally complex spiro multi heterocyclic skeletons in good yields (up to 87% 90%, respectively) with excellent diastereoselectivities >25:1 dr). In particular, the switchable annulation reactions are controlled by tuning hydroxyl protecting group on MBH adduct deliver structural diverse spiro[indene-2,2'-[1,3]oxazino[2,3-a]isoquinoline] spiro[indene-2,1'-pyrrolo[2,1-a]isoquinoline], respectively. Furthermore, relative configuration chemical structure two kinds cycloadducts were confirmed through X-ray diffraction analysis.

Language: Английский

Citations

6
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

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2252 - 2256

Published: April 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.

Language: Английский

Citations

1
Asymmetric Construction of Bis‐Spirocyclic Pyrazolones Bearing Vicinal Quaternary Carbon Centers DOI
Mengjie Yang,

Aiqi Xue,

Xingfu Wei

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)

Published: April 8, 2024

Abstract A catalytic asymmetric (3+2) cyclization of pyrazolone‐based MBH adducts with alkylidenyl isoxazolones was presented by using DMAP‐derived chiral catalyst, affording bis‐spirocyclic pyrazolones bearing vicinal all‐carbon quaternary stereocenters within an imbedded cyclopentene ring scaffold in good yields excellent stereoselectivities under mild conditions.

Language: Английский

Citations

1