De novo synthesis of atropisomeric benzofurans via Cu/SPDO complex catalyzed asymmetric formal [3 + 2] annulation DOI

Fan‐Xiao Meng,

Xingyu Wang,

Ka Lu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 9, 2024

Language: Английский

Enantioselective synthesis of molecules with multiple stereogenic elements DOI Creative Commons
Arthur Gaucherand, Expédite Yen‐Pon,

Antoine Domain

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(22), P. 11165 - 11206

Published: Jan. 1, 2024

This review explores the fascinating world of molecules featuring multiple stereogenic elements, unraveling different strategies designed over years for their enantioselective synthesis.

Language: Английский

Citations

13

Organocatalytic Atroposelective Construction of Pentatomic Heterobiaryl Diamines through Arylation of 5-Aminoisoxazoles with Azonaphthalenes DOI
Weiwei Luo, Huanhuan Guo,

Qiu Xue-ying

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2564 - 2568

Published: March 21, 2024

An efficient catalytic asymmetric Michael-type reaction of azonaphthalenes with 5-aminoisoxazoles has been developed. The was based on the utilization a chiral phosphoric acid as catalyst, delivering large panel axially heterobiaryl diamines in generally good yields excellent enantioselectivities. gram-scale and postmodification product demonstrated their potentials synthesis catalysts ligands. This approach not only provides useful method for construction pentatomic scaffolds but also offers new members to diamine family promising applications synthetic medicinal chemistry.

Language: Английский

Citations

4

Sc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks DOI
Ke Xu, Heping Li,

Yan‐Ling Ji

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1006 - 1011

Published: Jan. 16, 2025

Herein, we introduce a scandium-catalyzed synthetic strategy that provides access to diverse and functionalized array of cyclobutene frameworks adorned with quaternary carbon center. This approach broadens the repertoire 2-alkynylnaphthols alkenes, offering versatile platform for construction complex molecular architectures. The asymmetric catalytic [2 + 2] cycloaddition reaction demonstrates wide substrate scope an impressive functional group tolerance, yielding products high efficiency, up 97% yield, excellent enantiomeric excess 97%. simplicity scaling this process, coupled ease converting these into variety substituted products, significantly enhances utility method.

Language: Английский

Citations

0

Synthesis of 1,5-Diamino-Substituted 1,3-Dienes via Rhodium(II)-Catalyzed Tandem Reactions of 1-Cyclopropylethylarenes DOI

X.‐F. LIN,

Beiqi Yang,

Yuanhua Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Herein, (E,E)-1,5-diamino-1,3-dienes are stereoselectively synthesized from substituted aryl derivatives via a rhodium(II)-catalyzed C(sp3)-H functionalization involving cascade of cyclopropane ring expansion, cyclobutene formation, to 1,3-diene conversion, and regioselective diamination. Mechanistic studies show this one-pot process proceeds through hydrogen atom transfer (HAT), radical-polar crossover (RPC), elimination, electrocyclic ring-opening, radical addition, underscoring rhodium(II)'s role in radical-mediated catalysis beyond traditional rhodium(II) nitrenoid chemistry.

Language: Английский

Citations

0

Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating DOI

Wei-Le Li,

Bao-Yang Liu,

Chunmei Li

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 138, P. 154962 - 154962

Published: Feb. 16, 2024

Language: Английский

Citations

2

Enantioselective Friedel‐Crafts Reaction of ortho‐Alkynylnaphthols with Naphthofurans: Synthesis of Polysubstituted Axially Chiral Styrenes DOI
Wenxuan Zhang, Jiaying Sun, Daoshan Yang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2710 - 2714

Published: May 7, 2024

Abstract Herein, we report a chiral Brønsted acid‐catalyzed enantioselective Friedel‐Crafts reaction of ortho ‐alkynylnaphthols with various naphthofurans, realizing the asymmetric synthesis axially styrenes naphthofurans in 67 to 93% yield and 34 96% ee.

Language: Английский

Citations

1

Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides DOI
Xin‐Qi Zhu,

Hai‐Yu Yang,

Long‐Wu Ye

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(49)

Published: June 26, 2024

Vinylidene ortho-quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction last decade, thus drawn considerable concentrations on account of practical application construction enantiomerically pure functional organic molecules. However, comparison well established chiral Brønsted base-catalyzed via VQMs, acid-catalyzed is rarely studied there no systematic summary date. In this review, we summarize recent advances VQMs according three types reactions: a) intermolecular nucleophilic addition VQMs; b) cycloaddition c) intramolecular cyclization VQMs. Finally, put forward remained challenges opportunities for potential breakthroughs area.

Language: Английский

Citations

0

Proline-based Organocatalyst for the Synthesis of Arylidene Benzofuranone Intermediates Enabling the Construction of Aurone-derived Azadienes DOI
Azhaar T. Alsaggaf, Mostafa Sayed, Ahmed I. A. Soliman

et al.

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 29(2), P. 127 - 134

Published: Aug. 26, 2024

: Organocatalysis has been recognized as a part of chemical research for long time, and it gained significant attention in catalysis recent decades. Amine catalyst is substantial type organocatalysis, successively employed the activation carbonyl compounds. This manuscript delves into exploration proline-based organocatalyst synthesis arylidene benzofuranone intermediates, critical step that facilitates subsequent construction aurone-derived azadienes. In this work, we successfully reported intermediates through Aldol condensation with different aldehydes enabled by proline-derived organic catalysts. To achieve strategy, six examples amine organocatalysts (A1-A6) were evaluated to showcase optimal transformation. Moreover, further interesting azadiene substrates its reaction TsNH2. Notably, using A6 resulted delivery product best yield (94% isolated yield). Under optimized conditions, aromatic heterocyclic containing effectively tolerated generate corresponding which converted products high excellent yield. The claimed structures confirmed spectral analysis.

Language: Английский

Citations

0

De novo synthesis of atropisomeric benzofurans via Cu/SPDO complex catalyzed asymmetric formal [3 + 2] annulation DOI

Fan‐Xiao Meng,

Xingyu Wang,

Ka Lu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 9, 2024

Language: Английский

Citations

0