NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives DOI

Hong Ji,

Juan Zou, Chengli Mou

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(42), P. 6351 - 6354

Published: Jan. 1, 2023

An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp3 (C-H) bond activation 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that products exhibit superior in vitro bioactivities against two plant pathogens commercial Bismerthiazol (BT) Thiodiazole Copper (TC).

Language: Английский

Oxidative N‐Heterocyclic Carbene Catalysis DOI Creative Commons
Carmela De Risi, Arianna Brandolese, Graziano Di Carmine

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 29(4)

Published: Oct. 7, 2022

N-Heterocyclic carbene (NHC) catalysis is a by now consolidated organocatalytic platform for number of synthetic (asymmetric) transformations via diverse reaction modes/intermediates. In addition to the typical umpolung processes involving acyl anion/homoenolate equivalent species, implementation protocols under oxidative conditions greatly expands possibilities this methodology. Oxidative NHC-catalysis allows and oxygenative through specific manipulations Breslow-type species depending upon oxidant used (external or O

Language: Английский

Citations

39

N-Heterocyclic carbene-catalyzed enantioselective (dynamic) kinetic resolutions and desymmetrizations DOI
Yi Zhang, Hui Cai, Xiuhai Gan

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 482 - 511

Published: Sept. 11, 2023

Language: Английский

Citations

39

Catalytic N-Acylation for Access to N–N Atropisomeric N-Aminoindoles: Choice of Acylation Reagents and Mechanistic Insights DOI

Chaoyang Song,

Pang Chen,

Youlin Deng

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 6926 - 6935

Published: April 18, 2024

The synthesis of N–N axial compounds containing aromatic acyl amides using common acylation reagents remains challenging. We describe a highly atropenantioselective N-aminoindoles axes. A chiral cyclic isothiourea is used as the sole organic catalyst in transformation N-acylation reaction. Aroyl chlorides have been to construct atropisomeric through N-acylation. N-aminoindole products, which bear stereogenic axes, were synthesized with high yields and enantioselectivities. Some enantiopure products exhibited promising antibacterial activities against plant pathogens.

Language: Английский

Citations

10

Recent advances in metal-free catalytic enantioselective higher-order cycloadditions DOI Creative Commons
Bei Zhang, Jian Wang

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1824 - 1842

Published: Jan. 1, 2024

In this review, we briefly summarize the recent research progress in enantioselective higher-order cycloadditions, focusing on preparation of medium-sized and multicyclic chiral molecules by metal-free catalysis.

Language: Английский

Citations

9

Bridging the information gap in organic chemical reactions DOI
Malte L. Schrader, Felix Schäfer,

Felix Schäfers

et al.

Nature Chemistry, Journal Year: 2024, Volume and Issue: 16(4), P. 491 - 498

Published: March 28, 2024

Language: Английский

Citations

9

NHC-catalyzed covalent activation of heteroatoms for enantioselective reactions DOI Creative Commons
Runjiang Song, Zhichao Jin, Yonggui Robin

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(14), P. 5037 - 5043

Published: Jan. 1, 2021

Covalent activation of heteroatoms enabled by N-heterocyclic carbene (NHC) organic catalysts for enantioselective reactions is evaluated and summarized in this review.

Language: Английский

Citations

55

Diarylureas: New Promising Small Molecules against Streptococcus mutans for the Treatment of Dental Caries DOI Creative Commons
Domenico Iacopetta, Jessica Ceramella, Alessia Catalano

et al.

Antibiotics, Journal Year: 2023, Volume and Issue: 12(1), P. 112 - 112

Published: Jan. 7, 2023

Dental caries is a biofilm-mediated disease that represents worldwide oral health issue. Streptococcus mutans has been ascertained as the main cariogenic pathogen responsible for human dental caries, with high ability to form biofilms, regulated by quorum sensing. Diarylureas represent class of organic compounds show numerous biological activities, including antimicrobial one. Two small molecules belonging this class, specifically diphenylureas, BPU (1,3-bis[3,5-bis(trifluoromethyl)phenyl]urea) and DMTU (1,3-di-m-tolyl-urea), showed interesting results in studies regarding activity against bacterium S. mutans. Since there are not many antimicrobials used prevention treatment further on these two other diarylureas may be useful design new effective agents generally low cytotoxicity.

Language: Английский

Citations

17

Recent Advances in Metal‐ and Organocatalyzed Asymmetric Functionalization of Pyrroles DOI
Biplob Borah, Kartikey Dhar Dwivedi, L. Raju Chowhan

et al.

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(11), P. 2709 - 2762

Published: Sept. 18, 2021

Abstract The wide occurrence of pyrroles in natural products and pharmaceuticals calls for novel synthetic methodologies the efficient synthesis enantiopure pyrroles. Owing to their highly reactive nature wide‐ranging chemical landscape, enormous efforts have been dedicated not only but also development reactions using them as a platform utilization stereocontrolled diverse molecules. In sharp contrast extensive studies devoted toward indoles, asymmetric functionalization was less explored. Nevertheless, attractiveness selective access product analogy, medicinally useful architectures witnessed tremendous growth last few years. Their effectiveness under both metal‐ organocatalytic conditions currently encompasses vast majority enantioselective transformations. This review article aims present comprehensive overview catalytic C−H well N−H reported from 2010 now.

Language: Английский

Citations

34

Higher-order cycloadditions in the age of catalysis DOI Creative Commons
Nicolaj Inunnguaq Jessen, David McLeod, Karl Anker Jørgensen

et al.

Chem, Journal Year: 2021, Volume and Issue: 8(1), P. 20 - 30

Published: Nov. 22, 2021

Language: Английский

Citations

34

Construction of Tetrasubstituted Silicon-Stereogenic Silanes via Conformational Isomerization and N-Heterocyclic Carbene-Catalyzed Desymmetrization DOI
Mali Zhou, Jianjian Liu, Rui Deng

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(13), P. 7781 - 7788

Published: June 16, 2022

Disclosed here is a catalytic strategy for asymmetric access to chiral tetrasubstituted silicon-stereogenic silanes. Our reaction starts with (covalently) symmetric silane bearing two aldehyde moieties as the substrate. Single-crystal structural analysis shows that substrate exists racemate of conformational enantiomers because presence Si/O weak interaction. Mechanistic studies assisted by DFT calculation indicate can readily isomerize each other, and one favorably activated N-heterocyclic carbene catalyst via an overall desymmetrization process eventually afford optically enriched silanes products. silanes' products be transformed diverse set silicon stereogenic functional molecules.

Language: Английский

Citations

26