Preparation of Ionic Liquid Supported Organocatalysts for the Synthesis of Stereoselective (R)-9-Methyl-5(10)-Octaline-1,6-Dione DOI
Vivek Srivastava

Current Organocatalysis, Journal Year: 2022, Volume and Issue: 10(1), P. 26 - 33

Published: Nov. 4, 2022

: The synthesis of Proline-2-triethyl-ethylamide hexafluorophosphate (ILPA-PF6) (with 96% yield) and further the application during (R)-9-Methyl-5(10)-octaline-1,6-dione (Wieland-Miescher ketone molecule) are defined in this manuscript. suggested protocol signifies one most efficient methods for these flexible chiral building blocks good yield. evident solubility ionic liquids allows straightforward isolation (R)-9-Methyl- 5(10)-octaline-1,6-dione product from reaction mass. Additionally, six times catalyst recycling was considered main conclusion proposed procedure. Background: WMK starts with Michael Addition step, where α, β- unsaturated reacts 2-methyl-1,3-cyclohexanedione followed by nucleophilic attack produces triketone. Further, isolated triketone goes to intramolecular Aldol Condensation, (in Robinson Annulation cascade) get an enolate. Later, dehydrogenation enolate (to expel hydroxide ion) desired Wieland Miescher Ketone above conventional method suffers several drawbacks like a slow rate, requirement high boiling point solvent systems, low Objective:: To prepare liquid-supported organocatalysts stereoselective (R)- 9-Methyl-5(10)-octaline-1,6-dione Method: This report summarizes its triethyl salt-supported prolinebased as recyclable highly asymmetric Wieland-Miescher ((R)-9-Methyl-5(10)-octaline-1,6-dione). An proline (as catalyst) is equipped basic significantly acidic amide moiety promote synchronously having specialty liquid could be easy separate recycle. Results:: simply molecule yield enantioselectivity minimal ether washing. During reaction, loading i.e., 0.5 g found enough attain maximum 2 hours. Furthermore, observed 6 significant element catalytic method. Conclusion:: extremely dynamic enantioselective ILPA-PF6 approach demonstrated report. modified after characterization use subsequent aldol

Language: Английский

New advances in asymmetric organocatalysis II DOI Creative Commons
Radovan Šebesta

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 766 - 769

Published: April 15, 2025

Language: Английский

Citations

0
Asymmetric photoreactions catalyzed by chiral ketones DOI Creative Commons

Baoji Bian,

Yulong Liu, Lixin Qiao

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(4), P. 2874 - 2889

Published: Jan. 1, 2025

Asymmetric catalytic reactions are essential for synthesizing chiral drugs and fine chemicals, with their stereoselectivity influenced significantly by interactions between catalysts substrates.

Language: Английский

Citations

0
The Importance of Organocatalysis (Asymmetric and Non‐Asymmetric) in Agrochemicals DOI
Sandeep Kumar Sharma

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(12)

Published: March 22, 2023

Abstract Organocatalysis has been well established and documented for the asymmetric non synthesis of pharmaceuticals, natural products fine chemicals. However, relatively a few reports have reported regarding chiral or achiral agrochemicals while using organocatalysis. With continuous growing interest in modern agricultural chemistry, this review will provide comprehensive overview some important on successful applications organocatalysts agrochemicals. The summarized organocatalytic approach both non‐asymmetric such chemicals with respect to academic industrial aspects.

Language: Английский

Citations

2
Preparation of Ionic Liquid Supported Organocatalysts for the Synthesis of Stereoselective (R)-9-Methyl-5(10)-Octaline-1,6-Dione DOI
Vivek Srivastava

Current Organocatalysis, Journal Year: 2022, Volume and Issue: 10(1), P. 26 - 33

Published: Nov. 4, 2022

: The synthesis of Proline-2-triethyl-ethylamide hexafluorophosphate (ILPA-PF6) (with 96% yield) and further the application during (R)-9-Methyl-5(10)-octaline-1,6-dione (Wieland-Miescher ketone molecule) are defined in this manuscript. suggested protocol signifies one most efficient methods for these flexible chiral building blocks good yield. evident solubility ionic liquids allows straightforward isolation (R)-9-Methyl- 5(10)-octaline-1,6-dione product from reaction mass. Additionally, six times catalyst recycling was considered main conclusion proposed procedure. Background: WMK starts with Michael Addition step, where α, β- unsaturated reacts 2-methyl-1,3-cyclohexanedione followed by nucleophilic attack produces triketone. Further, isolated triketone goes to intramolecular Aldol Condensation, (in Robinson Annulation cascade) get an enolate. Later, dehydrogenation enolate (to expel hydroxide ion) desired Wieland Miescher Ketone above conventional method suffers several drawbacks like a slow rate, requirement high boiling point solvent systems, low Objective:: To prepare liquid-supported organocatalysts stereoselective (R)- 9-Methyl-5(10)-octaline-1,6-dione Method: This report summarizes its triethyl salt-supported prolinebased as recyclable highly asymmetric Wieland-Miescher ((R)-9-Methyl-5(10)-octaline-1,6-dione). An proline (as catalyst) is equipped basic significantly acidic amide moiety promote synchronously having specialty liquid could be easy separate recycle. Results:: simply molecule yield enantioselectivity minimal ether washing. During reaction, loading i.e., 0.5 g found enough attain maximum 2 hours. Furthermore, observed 6 significant element catalytic method. Conclusion:: extremely dynamic enantioselective ILPA-PF6 approach demonstrated report. modified after characterization use subsequent aldol

Language: Английский

Citations

0