Nucleophilic Addition of Ethyl 3-Bromodifluoromethyl-3-benzyloxyacrylate to Imines: An Effective Entry to Novel gem-Difluorinated Amino Esters and Their Derivatives.

ChemInform ◽  
2006 ◽  
Vol 37 (24) ◽  
Author(s):  
Weimin Peng ◽  
Jingwei Zhao ◽  
Ping He ◽  
Shizheng Zhu
Keyword(s):  
Nucleophilic Addition ◽  
Amino Esters

scholarly journals Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters

2017 ◽  
Vol 15 (14) ◽  
pp. 2993-3005 ◽  
Author(s):  
José A. Carmona ◽  
Gonzalo de Gonzalo ◽  
Inmaculada Serrano ◽  
Ana M. Crespo-Peña ◽  
Michal Šimek ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Keto Esters ◽  
Amino Esters ◽  
Azoxy Compounds

New carbohydrate based organocatalysts have been developed for the asymmetric nucleophilic addition of formaldehyde tert-butylhydrazone to α-keto esters.

Unexpected and intriguing reactivity of α-imino esters and iminium salts

2006 ◽  
Vol 78 (10) ◽  
pp. 1867-1876 ◽  
Author(s):  
Makoto Shimizu
Keyword(s):  
Benzoyl Peroxide ◽  
Nucleophilic Addition ◽  
Coupling Reaction ◽  
Grignard Reagents ◽  
Tandem Reaction ◽  
Amino Esters ◽  
Iminium Salts ◽  
Iminium Salt ◽  
Oxidative Removal ◽  
Imino Esters

An intriguing umpolung of the reactivity of imines possessing electron-withdrawing groups was observed. For example, N-alkylation-coupling reaction of the imines derived from glyoxylates was conducted with dialkylaluminum chloride in acetonitrile to give N-monoalkylated 1,2-diamines in good yields. On treatment of various α-imino esters with organoaluminum reagents and allyltributyltin in the presence of benzoyl peroxide (BPO), the tandem reaction proceeded to give the N-alkylation/C-allylation products in good yields. Diethyl 2-[N-(p-methoxyphenyl)imino]-malonate underwent amination reactions with alkyl Grignard reagents to give N-alkylation products in good yields. The obtained N-alkylation products were readily converted into N-alkyl-p-anisidines by the oxidative removal of the malonate moiety. In order to enhance the reactivity of imines, an iminium salt was prepared using the oxidation of amino ketene silyl acetal with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), and the subsequent nucleophilic addition to this iminium species proceeded to afford α-amino esters in good yields.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Recent Progress in Chemosensors Using Aldehyde-bearing Fluorophores for the Detection of Specific Analytes and their Bioimaging

2019 ◽  
Vol 26 (21) ◽  
pp. 4003-4028 ◽  
Author(s):  
Fangjun Huo ◽  
Yaqiong Zhang ◽  
Caixia Yin
Keyword(s):  
Biomedical Research ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Biological Imaging ◽  
Tissue Imaging ◽  
Fluorescence Probes ◽  
Biological Applications ◽  
Convenient Procedure ◽  
Nucleophilic Mechanism

In recent years, aldehyde-appended fluorescence probes have attracted increasing attention. Fluorescent biological imaging includes many modern applications for cell and tissue imaging in biomedical research. Meanwhile, the nucleophilic mechanism is a very simple and convenient procedure for the preparation of aldehyde-sensing probes. This tutorial review focuses on aldehyde-bearing chemosensors based on nucleophilic addition mechanism with biological applications.

Formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycine anion

1989 ◽  
Vol 54 (2) ◽  
pp. 440-445 ◽  
Author(s):  
Vladimír Macháček ◽  
Alexandr Čegan ◽  
Miloš Sedlák ◽  
Vojeslav Štěrba
Keyword(s):  
Nmr Spectroscopy ◽  
Dimethyl Sulfoxide ◽  
Equilibrium Constant ◽  
Mole Fraction ◽  
Nucleophilic Addition ◽  
Adduct Formation ◽  
First Case ◽  
C Nmr

The intramolecular nucleophilic addition of N-methyl-N-(2,4,6-trinitrophenyl)glycine anion in methanol-dimethyl sulfoxide mixtures produces spiro[(3-methyl-5-oxazolidinone)-2,1'-(2',4',6'-trinitrobenzenide)]. The spiro adduct has been identified by means of 1H and 13C NMR spectroscopy. This is the first case when the formation of a Meisenheimer adduct with carboxylate ion is observed. Logarithm of the equilibrium constant of adduct formation increases linearly with the mole fraction of dimethyl sulfoxide in its mixture with methanol.

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