Chiral C2-symmetric 2,5-disubstituted pyrrolidine derivatives as catalytic chiral ligands in the reactions of diethylzinc with aryl aldehydes

1998 ◽  
pp. 2547-2552 ◽  
Author(s):  
Min Shi ◽  
Yukihiro Satoh ◽  
Yukio Masaki
Keyword(s):  
Chiral Ligands ◽  
Aryl Aldehydes

Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes

2015 ◽  
Vol 26 (2-3) ◽  
pp. 152-157 ◽  
Author(s):  
Saffet Celik ◽  
Murat Cakici ◽  
Hamdullah Kilic ◽  
Ertan Sahin
Keyword(s):  
Chiral Ligands ◽  
Aryl Aldehydes

Synthesis of Axially Chiral 2,2’-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution

2020 ◽  
Author(s):  
Ziqing Zuo ◽  
Raphael Kim ◽  
Donald Watson
Keyword(s):  
Optical Resolution ◽  
Chiral Ligands ◽  
Chiral Auxiliaries ◽  
Axially Chiral ◽  
Ullmann Coupling

<div><p>We report an asymmetric Ullmann-type homocoupling of <i>ortho-</i>(iodo)arylphosphine oxides and <i>ortho</i>-(iodo)arylphosphonates that results in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates in good yields and excellent enantioselectivities. These products are readily converted to enantioenriched biaryl bisphosphines without need for chiral auxiliaries or optical resolution. This process provides a straightforward and practical route for the development of previously uninvestigated atroposelective biaryl bisphosphine ligands.</p></div>

Nickel-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Hydrazones

2019 ◽  
Author(s):  
Leiyang Lv ◽  
Dianhu Zhu ◽  
Zihang Qiu ◽  
Jianbin Li ◽  
Chao-Jun Li
Keyword(s):  
Catalytic Method ◽  
Unsaturated Hydrocarbons ◽  
Carbon Nucleophiles ◽  
Aryl Aldehydes ◽  
Aldehydes And Ketones ◽  
Sterically Hindered

Hydroalkylation of unsaturated hydrocarbons with unstablized carbon nucleophiles is difficult and remains a major challenge. The disclosed examples so far mainly focused on the involvement of heteroatom and/or stabilized carbon nucleophiles as efficient reaction partners. Reported here is an unprecedented regioselective nickel-catalyzed hydroalkylation of 1,3-dienes with hydrazones, generated in situ from abundant aryl aldehydes and ketones and acted as both the sources of unstabilized carbanions and hydride. With this strategy, both terminal and sterically hindered internal dienes are hydroalkylated efficiently in a highly selective manner, thus providing a novel and reliable catalytic method to construct challenging C(sp3)-C(sp3) bonds.

Novel Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation/ Asymmetric Tsuji-Trost Reaction: A Review

2019 ◽  
Vol 23 (11) ◽  
pp. 1168-1213 ◽  
Author(s):  
Samar Noreen ◽  
Ameer Fawad Zahoor ◽  
Sajjad Ahmad ◽  
Irum Shahzadi ◽  
Ali Irfan ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Enantioselective Synthesis ◽  
Chiral Ligands ◽  
Allylic Alkylation ◽  
Research Groups ◽  
Asymmetric Allylic Alkylation ◽  
Catalytic Potential ◽  
Long Time ◽  
Palladium Catalyzed ◽  
Alkylation Reactions

Background: Asymmetric catalysis holds a prestigious role in organic syntheses since a long time and chiral inductors such as ligands have been used to achieve the utmost desired results at this pitch. The asymmetric version of Tsuji-Trost allylation has played a crucial role in enantioselective synthesis. Various chiral ligands have been known for Pdcatalyzed Asymmetric Allylic Alkylation (AAA) reactions and exhibited excellent catalytic potential. The use of chiral ligands as asymmetric inductors has widened the scope of Tsuji-Trost allylic alkylation reactions. Conclusion: Therefore, in this review article, a variety of chiral inductors or ligands have been focused for palladium catalyzed asymmetric allylic alkylation (Tsuji-Trost allylation) and in this regard, recently reported literature (2013-2017) has been described. The use of ligands causes the induction of enantiodiscrimination to the allylated products, therefore, the syntheses of various kinds of ligands have been targeted by many research groups to employ in Pd-catalyzed AAA reactions.

Synthesis and Characterization of a Novel Ionic Liquid Based on N,N,N,N-tetramethylethylenediamine and its Application in the Synthesis of 1,8-dioxo-octahydro Xanthenes

2018 ◽  
Vol 21 (7) ◽  
pp. 526-532 ◽  
Author(s):  
Zahra Abdi Piralghar ◽  
Mohammad Mahmoodi Hashemi ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Chlorosulfonic Acid ◽  
Solvent Free ◽  
Aryl Aldehydes ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Aryl Aldehyde ◽  
High Yields

Aim and Objective: In this work, we synthesized and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N’, N’-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis. Materials and Methods: Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin layer of chromatography (ethyl acetate/n-hexane = 1/5). All products were characterized as the basis of their spectra data and melting point by comparison with those reported in the literature. Results: The prepared ionic liquid was successfully applied in the synthesis of 1, 8-dioxooctahydroxanthenes in good to high yields on the reaction of aryl aldehyde and dimedone at 120oC under solvent-free conditions. Conclusion: This research demonstrates that the catalyst is impressive for 1, 8-dioxo-octahydroxanthenes synthesis under solvent-free conditions.

Novel Synthesis of 4-Benzylidene-2-((1-phenyl-3,4-dihydroisoquinoline-2(1H)-yl)methyl) oxazol-5(4H)-one Derivatives Using 1,2,3,Tetrahydroisoquinoline and their Antimicrobial Activity

2020 ◽  
Vol 17 (5) ◽  
pp. 396-403
Author(s):  
Nalla Krishna Rao ◽  
Tentu Nageswara Rao ◽  
Botsa Parvatamma ◽  
Y. Prashanthi ◽  
Ravi Kumar Cheedarala
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Acetic Acid ◽  
Sodium Acetate ◽  
Good Activity ◽  
Activity Profile ◽  
Aryl Aldehydes ◽  
Chemical Structures ◽  
Novel Synthesis ◽  
Target Molecules

Aims: A series of six 4-benzylidene-2-((1-phenyl-3,4-dihydro isoquinoline-2(1H)-yl)methyloxazol- 5(4H)-one derivatives were synthesized by condensation of substituted aryl aldehydes with 2-(2-(1-phenyl-3,4- dihydro isoquinoline-2(1H)-acetamido)acetic acid in the presence of sodium acetate, acetic anhydride and zinc oxide as catalysts. Background: Novel Synthesis of 4-Benzylidene-2-((1-phenyl-3,4-dihy droisoquinoline-2(1H)-yl)methyl)oxazol- 5(4H)-one derivatives using 1,2,3,Tetrahydroisoquinoline and their antimicrobial activity. Objective: The title compounds can be synthesized from 1,2,3,4-tetrahydroisoquinoline. Methods: The target molecules, i.e., 4-benzylidene-2-((1-phenyl-3, 4-dihydro isoquinoline-2(1H)-yl) methyl) oxazol-5(4H)-one derivatives (8a-8f) have been synthesized from 1,2,3,4-tetrahydroisoquinoline which was prepared from benzoic acid in few steps. Results: All the six compounds were evaluated based on advanced spectral data (1H NMR, 13C NMR & LCMS), and the chemical structures of all compounds were determined by elemental analysis. Conclusion: Antibacterial activity of the derivatives was examined for the synthesized compounds and results indicate that compound with bromine substitution has a good activity profile.

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