scholarly journals Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7399
Author(s):  
Lucilla Favero ◽  
Andrea Menichetti ◽  
Cosimo Boldrini ◽  
Lucrezia Margherita Comparini ◽  
Valeria Di Bussolo ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Addition Reaction ◽  
Computational Studies ◽  
Reaction Conditions ◽  
Ring Opening Reactions ◽  
Computational Data ◽  
Nucleophilic Addition Reaction ◽  
Direct Preparation

The possibility to form new C–B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2pin2) in a regioselective nucleophilic addition reaction under copper catalysis.

Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl Halides to Aryl Ketones for the Synthesis of Benzofuran Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Chen-Liang Deng ◽  
Xiao-Rui Zhu
Keyword(s):  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Aryl Halides ◽  
Reaction Conditions ◽  
Aryl Ketones ◽  
Nucleophilic Addition Reaction ◽  
Standard Reaction

AbstractA nickel-catalyzed intramolecular nucleophilic addition reaction of aryl halides to aryl ketones for the formation of benzofuran derivatives has been developed. A number of substrates bearing electron-donating or electron-withdrawing groups were subjected to the standard reaction conditions, giving the corresponding products in moderate to good yields.

Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1–C9 and C10–C24 Fragments

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 663-675
Author(s):  
Pabbaraja Srihari ◽  
Ramakrishna Sayini
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Addition Reaction ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Ring Opening Reaction ◽  
Nucleophilic Addition Reaction ◽  
Convergent Approach ◽  
Key Steps

The C1–C9 and C10–C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira–Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still–Gennari olefination as key steps. A chiron approach , starting from readily available glucose diacetonide, was used to synthesize a key intermediate, and a convergent approach was adopted for the synthesis of the key C10–C24 fragment.

scholarly journals Monosuccinate ester of melampomagnolide B

2014 ◽  
Vol 70 (3) ◽  
pp. o372-o373
Author(s):  
Venumadhav Janganati ◽  
Narsimha Reddy Penthala ◽  
Nikhil Reddy Madadi ◽  
Sean Parkin ◽  
Peter A. Crooks
Keyword(s):  
Double Bond ◽  
Hydrogen Bonds ◽  
Nucleophilic Addition ◽  
Succinic Anhydride ◽  
Addition Reaction ◽  
Lactone Ring ◽  
Membered Ring ◽  
Reaction Conditions ◽  
Oxobutanoic Acid ◽  
Nucleophilic Addition Reaction

The title monosuccinate derivative of melampomagnolide B [systematic name: 4-(((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-5-yl)methoxy)-4-oxobutanoic acid], C19H24O7, was obtained from the reaction of melampomagnolide B with succinic anhydride under nucleophilic addition reaction conditions. The molecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The internal double bond in the ten-membered ring has thecisgeometry (i.e.it is theEisomer). The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O—H...O hydrogen bonds link the molecules into chains parallel to theb-axis direction.

Layer by layer assembled functionalized graphene oxide-based polymer brushes for superlubricity on steel-steel tribocontact

Soft Matter ◽  
2021 ◽  
Author(s):  
Suprakash Samanta ◽  
Rashmi Ranjan Sahoo
Keyword(s):  
Graphene Oxide ◽  
Nucleophilic Addition ◽  
Polymer Brushes ◽  
Addition Reaction ◽  
Layer By Layer ◽  
Functionalized Graphene ◽  
Covalent Functionalization ◽  
Functionalized Graphene Oxide ◽  
Nucleophilic Addition Reaction ◽  
Branched Polyethylenimine

Present study demonstrates a simple and multistep approach for the preparation of covalent functionalization of chemically prepared graphene oxide (GO) by branched polyethylenimine (PEI) through nucleophilic addition reaction to prepare...

Novel Ceric Ammonium Nitrate-Stabilized Maghemite Nanoparticles (CAN-γ-Fe2O3) for Ultrasound Assisted Synthesis of β-Amino Derivatives

2021 ◽  
Author(s):  
Anurag Kumar ◽  
Yifat Harel ◽  
Jean-paul Lellouche ◽  
Suman L. Jain
Keyword(s):  
Carbonyl Compounds ◽  
Addition Reaction ◽  
Ceric Ammonium Nitrate ◽  
Reusable Catalyst ◽  
Maghemite Nanoparticles ◽  
Reaction Conditions ◽  
Recyclable Catalysts ◽  
Nucleophilic Addition Reaction ◽  
Amino Derivatives ◽  
Positively Charged

Abstract Owing to their inherent features like smaller size and higher surface area exposed to reactants, nanoparticles have gained enormous interest and are extensively used as magnetically recyclable catalysts for various organic reactions. Herein, we report highly hydrophilic, non-aggregated, and strongly positively charged (ζ potential: +45.7 mV) ultra-small cerium cations/complexes- stabilized maghemite nanoparticles in water as an efficient and reusable nanoscaled magnetically active catalyst for the nucleophilic addition reaction of various amines with α,β-unsaturated carbonyl compounds to give corresponding β-amino derivatives under ultrasonic irradiation. The developed protocol provides several merits such as high product yields, mild reaction conditions, reusable catalyst and easy workup.

scholarly journals Catalytic Enantioselective Synthesis of 4-Amino-1,2,3,4-tetrahydropyridine Derivatives from Intramolecular Nucleophilic Addition Reaction of Tertiary Enamides

Synlett ◽  
2018 ◽  
Vol 30 (04) ◽  
pp. 483-487 ◽  
Author(s):  
Shuo Tong ◽  
Mei-Xiang Wang
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Catalysis ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Substrate Engineering ◽  
Nucleophilic Addition Reaction ◽  
Engineering Strategy ◽  
Acid Catalyzed

A general and efficient method for the synthesis of highly enantiopure 4-amino-1,2,3,4-tetradydropyridine derivatives based on chiral phosphoric acid catalyzed intramolecular nucleophilic addition of tertiary enamides to imines has been developed. We have also demonstrated a substrate engineering strategy to significantly improve the enantioselectivity of asymmetric catalysis

Nucleophilic addition reaction of aromatic compounds with α-chloroglycidates in the presence of Lewis acid

Tetrahedron ◽  
2003 ◽  
Vol 59 (10) ◽  
pp. 1781-1790 ◽  
Author(s):  
Jing-Rong Lin ◽  
Aidar T Gubaidullin ◽  
Vakhid A Mamedov ◽  
Sadao Tsuboi
Keyword(s):  
Lewis Acid ◽  
Aromatic Compounds ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Nucleophilic Addition Reaction

Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 7-12 ◽  
Author(s):  
Ye Zhang ◽  
Lei Zhang ◽  
Xiangbing Qi
Keyword(s):  
Total Synthesis ◽  
Common Core ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Synthetic Strategy ◽  
Nucleophilic Addition Reaction

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

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