Creation of bispiro[pyrazolone-3,3′-oxindoles] via a phosphine-catalyzed enantioselective [3 + 2] annulation of the Morita–Baylis–Hillman carbonates with pyrazoloneyldiene oxindoles DOI
Jing Zhang, Wai‐Lun Chan, Ligong Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2019, Volume and Issue: 6(13), P. 2210 - 2214

Published: Jan. 1, 2019

A [3 + 2] annulation between the Morita–Baylis–Hillman (MBH) carbonates and pyrazoloneyldiene oxindoles catalyzed by (S)-SITCP has been developed.

Language: Английский

Chiral Cyclopentadienyl Ligands: Design, Syntheses, and Applications in Asymmetric Catalysis DOI
Josep Mas‐Roselló, Ana G. Herraiz, B. Audic

et al.

Angewandte Chemie, Journal Year: 2020, Volume and Issue: 133(24), P. 13306 - 13332

Published: July 16, 2020

Abstract The creation of new chiral ligands capable providing high stereocontrol in metal‐catalyzed reactions is crucial modern organic synthesis. production bioactive molecules as single enantiomers increasingly required, and asymmetric catalysis with metal complexes constitutes one the most efficient synthetic strategies to access optically active compounds. Herein we offer a historical overview on development derivatives ubiquitous cyclopentadienyl ligand (Cp X ), detail their successful application broad range transformations. Those include functionalization challenging C−H bonds beyond, giving an extensive catalogue valuable molecules. A critical comparison existing families, design, synthesis, complexation different metals also provided. In addition, future research directions are discussed further enhance performance Cp enantioselective catalysis.

Language: Английский

Citations

51

Rhodium(III)-Catalyzed Enantioselective C–H Activation/Annulation of Ferrocenecarboxamides with Internal Alkynes DOI
Quannan Wang,

Yu‐Han Nie,

Chen‐Xu Liu

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(5), P. 3083 - 3093

Published: Feb. 21, 2022

Efficient synthesis of planar chiral ferrocene-fused heterocyclic molecules is challenging in asymmetric synthesis. Herein, we report an enantioselective C–H activation/annulation ferrocenecarboxamides with internal alkynes promoted by CpRh(III) catalysis. Trisubstituted Cp-derived Rh complexes are found to be enabling catalysts, which lead a broad substrate scope good functional group compatibility. Planar pyridone products obtained high yields (up 90%) excellent enantioselectivity 99% ee). Combined experimental and computational studies support the proposed reaction mechanism.

Language: Английский

Citations

35

The catalytic asymmetric synthesis of CF3-containing spiro-oxindole–pyrrolidine–pyrazolone compounds through squaramide-catalyzed 1,3-dipolar cycloaddition DOI
Cui Wang,

Dongwa Wen,

Hui Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(22), P. 5514 - 5519

Published: Jan. 1, 2019

Pharmaceutically important compounds were synthesized through the organocatalytic 1,3-dipolar cycloaddition reaction.

Language: Английский

Citations

53

Rhodium(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C(sp3)–H Alkylation of 8-Ethylquinolines with α,β-Unsaturated Carbonyl Compounds DOI

Long‐Tao Huang,

Seiya Fukagawa,

M. Kojima

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(21), P. 8256 - 8260

Published: Oct. 16, 2020

The enantioselective C–H alkylation of 8-ethylquinolines with enones or acrolein using a RhIII catalyst and chiral carboxylic acid is described. Under mild reaction conditions, binaphthyl-based enables the cleavage 8-ethylquinoline C(sp3)–H bond. obtained results demonstrate utility combination high-valent group 9 metal for activation subsequent C–C bond formation.

Language: Английский

Citations

49

Creation of bispiro[pyrazolone-3,3′-oxindoles] via a phosphine-catalyzed enantioselective [3 + 2] annulation of the Morita–Baylis–Hillman carbonates with pyrazoloneyldiene oxindoles DOI
Jing Zhang, Wai‐Lun Chan, Ligong Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2019, Volume and Issue: 6(13), P. 2210 - 2214

Published: Jan. 1, 2019

A [3 + 2] annulation between the Morita–Baylis–Hillman (MBH) carbonates and pyrazoloneyldiene oxindoles catalyzed by (S)-SITCP has been developed.

Language: Английский

Citations

46