Chiral Secondary Phosphine Oxide Ligands in Asymmetric Ni–Al Bimetallic Catalysis DOI

Mengying Xu,

Weiwei Xu, Mengchun Ye

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 2, 2024

Abstract Ligands play a key role in asymmetric transition‐metal catalysis. Among reported chiral ligands, readily available and air‐stable secondary phosphine oxide ligands are unique have aroused wide interest Ni−Al bimetallic catalysis, since they can act as bifunctional to ligate two metals for stronger synergism, greatly enhancing reactivity selectivity. Hence, this mini review we will focus on oxides their applications

Язык: Английский

Dynamic Kinetic Reductive Grignard-Type Addition for the Construction of Axial and Central Chirality DOI

Ya-Ping Shao,

Yong‐Min Liang

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 1147 - 1157

Опубликована: Янв. 3, 2025

This study describes a photoredox/cobalt dual-catalyzed asymmetric Grignard-type addition reaction, enabling the synthesis of axially chiral hexatomic (six–six) N-heterobiaryls bearing extra secondary alcohol unit via an efficient dynamic kinetic transformation racemic N-heterobiaryl triflate substrates. The conversion facilitated both photoredox and classical reductive reaction conditions exhibits good functional group tolerance, broad substrate scope, satisfactory stereoselectivity. Furthermore, control experiments density theory calculations provide preliminary mechanistic insights.

Язык: Английский

Процитировано

6

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

Antoine Domain

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер 53(22), С. 11165 - 11206

Опубликована: Янв. 1, 2024

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

Язык: Английский

Процитировано

17

Dearomative Addition-Hydrogen Autotransfer for Branch-Selective N-Heteroaryl C–H Functionalization via Ruthenium-Catalyzed C–C Couplings of Diene Pronucleophiles DOI
Jonathan Z. Shezaf, S. H. Lee,

Yhin Sarah Teoh

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Янв. 6, 2025

A novel mechanism for N-heteroaryl C–H functionalization via dearomative addition-hydrogen autotransfer is described. Upon exposure to the catalyst derived from RuHCl(CO)(PPh3)3 and Xantphos, dienes 1a–1g suffer hydroruthenation form allylruthenium nucleophiles that engage in addition-β-hydride elimination furnish branched products of C–C coupling 3a–3s 4a–4f. Oxidative cleavage isoprene adducts 3j, 3k, 3l, 3n followed by ruthenium-catalyzed dynamic kinetic asymmetric ketone reduction provides enantiomerically enriched N-heteroarylethyl alcohols 6a–6d and, therefrom, amines 7a–7d. Density functional theory calculations correlate experimentally observed regioselectivities with magnitude LUMO coefficients corroborate rate-determining addition. In presence 2-propanol trifluoroethanol, dearomatized pyrimidine 2a quinazoline 2n were isolated characterized.

Язык: Английский

Процитировано

2

Organocatalytic Atroposelective Fluorooxindole Addition to Coumarin Michael Acceptors DOI Creative Commons
Maria Bouda,

Grace E. Hana,

Dea Xhili

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Organocatalytic atropisomeric synthesis with fluorinated oxindoles and 4-halo-3-nitrocoumarins gives congested structures displaying a Csp2-Csp3 chirality axis an adjacent tetrasubstituted stereogenic carbon center good yields, up to 97% ee 41 : 1 dr. The scalable dehalogenative C-C bond formation is achieved under mild conditions commercially available urea catalyst.

Язык: Английский

Процитировано

2

Dual Catalytic C(sp2)–H Activation of Azaheterocycles toward C–N Atropisomers DOI
Juntao Sun, Yiyao Hu, Wen‐Ji He

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 3700 - 3710

Опубликована: Фев. 14, 2025

Язык: Английский

Процитировано

1

Rhodium-Catalyzed Atroposelective C–H Alkylation of 1-Aryl Isoquinoline Derivatives with Cyclopropanols DOI
Wenwen Zhang, Quannan Wang, Chao Zheng

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 4017 - 4024

Опубликована: Фев. 20, 2025

Язык: Английский

Процитировано

1

Recent advances in the catalytic asymmetric construction of axially chiral azole-based frameworks DOI
Weiwei Luo, Yu Zhang,

Meijun Ming

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(23), С. 6819 - 6849

Опубликована: Янв. 1, 2024

This review highlights recent advances in the atroposelective preparation of axially chiral azole derivatives, emphasizing mechanistic insights and synthetic applications development this class five-membered heterocyclic frameworks.

Язык: Английский

Процитировано

3

Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers DOI Creative Commons

Tian‐Jiao Han,

Qingxiang Yang, Jin‐Feng Hu

и другие.

JACS Au, Год журнала: 2024, Номер 4(11), С. 4445 - 4454

Опубликована: Окт. 14, 2024

The development of chiroptical molecular switches for chiral sensing, data communication, optical displays, logic gates, and asymmetric catalysis is currently a vibrant frontier science technology. Herein, we report practical artificial dynamic system based on 1,2-diaxial atropisomer. Organocatalytic parallel kinetic resolution allows the divergent synthesis two sets stereoisomers with vicinal C-C N-N axes from same racemic single-axis substrates. By simply varying configuration single catalyst, all four are accessible. successive conduction covalent unlocking/locking thermal-isomerization processes enables sequential switching between atropisomeric states electronic circular dichroism signal reversal, providing an example multistate switches.

Язык: Английский

Процитировано

3

P(═O)R2-Directed Asymmetric Catalytic C–H Olefination Leading to C–N Axially Chiral Targets DOI

Shengzhou Jin,

Yu Wang, Jun Yan

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 11, 2025

A novel P(═O)R2-directed asymmetric catalytic olefination has been developed, enabling efficient access to carbon–nitrogen axially chiral products with excellent yields (up 92%) and enantioselectivity 99% enantiomeric excess). The synergistic coordination of phosphine oxide functionality l-pGlu-OH the Pd metal center, serving as an directing group ligand, was key success this C–H functionalization system. reaction demonstrated a broad substrate scope, yielding 33 distinct C–N axial products. absolute configuration unambiguously confirmed via X-ray diffraction analysis. Additionally, three representative applications were showcased, involving reduction oxidation produce phosphines related derivatives. plausible cycle mechanism proposed, supported by detailed experimental studies. Aggregates in system identified aggregation-induced polarization experiments.

Язык: Английский

Процитировано

0

Mechanistic insights into facilitating reductive elimination from Ni(ii) species DOI

Bolin Qiao,

Fa-You Lin,

Dongmin Fu

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(62), С. 8008 - 8019

Опубликована: Янв. 1, 2024

Reductive elimination is a key step in Ni-catalysed cross-couplings, which often considered to result new covalent bonds. Due the weak oxidizing ability of Ni(II) species, reductive eliminations from centers are challenging. A thorough mechanistic understanding this process could inspire rational design coupling reactions. In article, we give an overview recent advances study species achieved by our group. Three possible models for were investigated and discussed, including direct elimination, electron density-controlled oxidation-induced elimination. Notably, requires high activation energy some cases. contrast, pathways can significantly enhance driving force accelerating formation The intricate reaction mechanisms each these thoroughly discussed systematically summarized paper. These computational studies showcase characteristics three hope that it will spur development cross-coupling

Язык: Английский

Процитировано

2