Diastereoselective Synthesis of Tetracyclic Tetrahydroquinoline Derivative Enabled by Multicomponent Reaction of Isocyanide, Allenoate, and 2-Aminochalcone DOI
Zhishuang Wang,

Youwen Fei,

Chongrong Tang

и другие.

Organic Letters, Год журнала: 2021, Номер 23(11), С. 4094 - 4098

Опубликована: Май 13, 2021

We report here a multicomponent protocol to assemble several polycyclic dihydropyran-fused tetrahydroquinoline structures with excellent diastereoselectivity. This procedure employs simple feedstocks accomplish series of diverse structures, which is difficult attain by traditional sequences.

Язык: Английский

Asymmetric dearomatization of 2-nitrobenzofurans by organocatalyzed one-step Michael addition to access 3,3′-disubstituted oxindoles DOI

Zhen-Zhen Ge,

Lei Yang, Yong You

и другие.

Chemical Communications, Год журнала: 2020, Номер 56(17), С. 2586 - 2589

Опубликована: Янв. 1, 2020

An efficient enantioselective dearomatization of 2-nitrobenzofurans was realized via an organocatalyzed one-step Michael addition process. This method provides a facile strategy to access range structurally diverse 3,3'-disubstituted oxindoles, which feature intriguing combination two privileged motifs including 3-pyrrolyl-substituted-oxindoles and 2,3-dihydrobenzofurans substructures, in excellent results.

Язык: Английский

Процитировано

31

Diastereoselective Construction of Cyclopropane-Fused Tetrahydroquinolines via a Sequential [4 + 2]/[2 + 1] Annulation Reaction DOI
Zhen‐Hua Wang,

Li‐Wen Shen,

Kexin Xie

и другие.

Organic Letters, Год журнала: 2020, Номер 22(8), С. 3114 - 3118

Опубликована: Апрель 7, 2020

A sequential [4 + 2]/[2 1] annulation of α-aryl vinylsulfoniums with 2-aminochalcones and 2-(2-aminobenzylidene)-1H-indene-1,3(2H)-dione is reported that affords a series cyclopropane-fused tetrahydroquinolines. The salient features this novel practical transformation include high efficiency, transition-metal-free nature, operational simplicity, outstanding functional group tolerance.

Язык: Английский

Процитировано

30

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides DOI Creative Commons
Pratibha Sharma, R. Gupta, Raj K. Bansal

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2021, Номер 17, С. 2585 - 2610

Опубликована: Окт. 18, 2021

Nitrogen-containing scaffolds are ubiquitous in nature and constitute an important class of building blocks organic synthesis. The asymmetric aza-Michael reaction (aza-MR) alone or tandem with other reaction(s) is synthetic tool to form new C–N bond(s) leading developing libraries diverse types bioactive nitrogen compounds. synthesis application a variety organocatalysts for accomplishing highly useful syntheses without causing environmental pollution compliance ‘Green Chemistry” has been landmark development the recent past. Application many these extended aza-MR during last two decades. present article overviews literature published 10 years concerning amines amides catalysed by organocatalysts. Both organocatalysts, i.e., those acting through non-covalent interactions working covalent bond formation have applied aza-MR. Thus, review includes examples wherein cinchona alkaloids, squaramides, chiral amines, phase-transfer catalysts bifunctional thioureas used, which activate substrates hydrogen formation. Most reactions accompanied high yields enantiomeric excesses. On hand, N-heterocyclic carbenes pyrrolidine derivatives such as iminium ions also included. Wherever possible, comparison made between efficacies various

Язык: Английский

Процитировано

26

Thiol-Triggered Tandem Dearomative Michael Addition/Intramolecular Henry Reaction of 2-Nitrobenzofurans: Access to Sulfur-Containing Polyheterocyclic Compounds DOI

Jun-Rui Zhuo,

Jian‐Qiang Zhao, Lei Yang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(13), С. 2623 - 2628

Опубликована: Март 24, 2024

An efficient dearomative cyclization of 2-nitrobenzofurans via a thiol-triggered tandem Michael addition/intramolecular Henry reaction has been developed. A range thiochromeno[3,2-b]benzofuran-11-ols and tetrahydrothieno[3,2-b]benzofuran-3-ols could be obtained in up to 99% yield >20:1 dr. The valuable thiochromone fused benzofurans prepared with the 2-mercaptobenzaldehyde reaction/rearomatization/oxidative dehydrogenation process one-pot two-step operation. mechanism for was tentatively proposed.

Язык: Английский

Процитировано

4

Phosphine-catalyzed dearomative (3 + 2) annulation of 2-nitrobenzofurans and nitrobenzothiophenes with allenoates DOI
Jian‐Qiang Zhao, Lei Yang, Yong You

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2019, Номер 17(21), С. 5294 - 5304

Опубликована: Янв. 1, 2019

An efficient Ph2PMe-catalyzed dearomative (3 + 2) annulation of 2-nitrobenzofurans, 2-nitrobenzothiophenes, and 3-nitrobenzothiophenes with allenoates is reported.

Язык: Английский

Процитировано

30

Catalytic Enantioselective Dearomatization/Rearomatization of 2-Nitroindoles to Access 3-Indolyl-3′-Aryl-/Alkyloxindoles: Application in the Formal Synthesis of Cyclotryptamine Alkaloids DOI
Wei‐Cheng Yuan, Xiaojian Zhou, Jian‐Qiang Zhao

и другие.

Organic Letters, Год журнала: 2020, Номер 22(18), С. 7088 - 7093

Опубликована: Авг. 28, 2020

The first catalytic enantioselective dearomatization/rearomatization of 2-nitroindoles triggered by the Michael addition 3-monosubstituted oxindoles was established. A wide range 3-indolyl-3'-alkyloxindoles (up to 99% yield, 97% ee) and 3-indolyl-3'-aryloxindoles 95% were obtained using an organocatalyst. This method provides unprecedented strategy access structurally diverse 3,3'-disubstituted bearing a sterically congested triaryl-containing all-carbon quaternary stereocenter. utility this approach verified formal synthesis cyclotryptamine alkaloids.

Язык: Английский

Процитировано

25

Dinuclear Zinc Catalyzed Enantioselective Dearomatization [3+2] Annulation of 2‐Nitrobenzofurans and 2‐Nitrobenzothiophenes DOI
Peng Zhou,

Yang Yi,

Yuan‐Zhao Hua

и другие.

Chemistry - A European Journal, Год журнала: 2021, Номер 28(2)

Опубликована: Окт. 29, 2021

The application of dinuclear zinc catalysts in a dearomatization reaction has been developed. Catalytic asymmetric [3+2] annulations 2-nitrobenzofurans or 2-nitrobenzothiophenes with CF3 -containing N-unprotected isatin-derived azomethine ylides catalyzed by are realized excellent diastereomer ratios (dr) >20 : 1 and enantiomeric excess (ee) up to 99 %. This protocol provides practical, straightforward access structurally diverse pyrrolidinyl spirooxindoles containing 2,3-fused-dihydrobenzofuran (or dihydrobenzothiphene) moiety, four contiguous stereocenters. Reactions can be performed on gram scale. absolute configuration products is confirmed X-ray single crystal structure analysis, possible mechanism proposed.

Язык: Английский

Процитировано

23

Squaramide Catalyzed Asymmetric Synthesis of Five‐ and Six‐Membered Rings DOI
Anup Biswas, Avisek Ghosh,

Rajat Shankhdhar

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 10(6), С. 1345 - 1376

Опубликована: Апрель 19, 2021

Abstract Chiral analogues of squaramides have been fruitful in organocatalyzed asymmetric reactions over last decade. Alongside other H‐bonding catalysts like ureas, thioureas: proved to be efficient for the formation acyclic and cyclic chiral molecules. A wide range molecules bearing multiple functionalities stereocenters synthesized by using several bifunctional as catalysts. These perform base utilizing basic N atom their extension help stereoinduction forming H‐bonds with suitable H‐bond acceptors. The present review focuses on assembling recent progresses synthesis five six membered rings promoted squaramides. handful articles published research groups documenting construction five‐ six‐membered part interesting complex molecular architectures. Different methodologies conventional formal cycloadditions or cascade engineered through assistance fabricate carbo‐ heterocycles. This also includes dual cooperative catalytic system which squaramide is one

Язык: Английский

Процитировано

21

Dearomatization of Nitro(hetero)arenes through Annulation DOI
Ning Wang, Jing Ren, Kaizhi Li

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(18)

Опубликована: Апрель 5, 2022

Abstract Dearomatization reactions employing simple aromatic compounds have showcased remarkable progress in the recent decade and emerged as one of most straightforward powerful tools for creation highly functionalized, three‐dimensional molecular frameworks commonly encountered medicinal chemistry life sciences. Among use, nitro(hetero)arenes, which feature a less pronounced character due to presence electron‐withdrawing nitro group, been extensively used different types dearomatization reactions. The dearomative annulation reaction serves versatile method construction complex polycyclic systems. This overview presents brief summary impressive advances nitro(hetero)arenes provides some inspirations future research.

Язык: Английский

Процитировано

16

Recent advances in the synthesis of benzo[b]thiophene fused polycyclic derivatives: Strategies and reactions DOI

Jiali Huang,

Wenyang Wang,

Lei Zhang

и другие.

Chinese Chemical Letters, Год журнала: 2022, Номер 34(6), С. 108003 - 108003

Опубликована: Ноя. 13, 2022

Язык: Английский

Процитировано

15