DFT Study on Amine-Mediated Ring-Opening Mechanism of α-Amino Acid N-Carboxyanhydride and N-Substituted Glycine N-Carboxyanhydride: Secondary Amine versus Primary Amine

2015 ◽  
Vol 119 (27) ◽  
pp. 7070-7074 ◽  
Author(s):  
Junhua Liu ◽  
Jun Ling
Keyword(s):  
Amino Acid ◽  
Secondary Amine ◽  
Primary Amine ◽  
Ring Opening ◽  
Dft Study

Regio-, Stereo- and Enantioselective α-Addition of Carbonyl Nucleo-philes to Allenamides Catalyzed by a Synergistic Copper/Enamine System

2020 ◽  
Author(s):  
Rémi Blieck ◽  
Sebastien Lemouzy ◽  
Marc Taillefer ◽  
Florian Monnier
Keyword(s):  
Catalytic System ◽  
Secondary Amine ◽  
Primary Amine ◽  
Synergistic Catalysis ◽  
Enantioselective Addition ◽  
Amine Catalysts

A dual copper/enamine catalytic system is found to enable an intermolecular enantioselective α-addition of various carbonyl nucleophiles to allenamides. Secondary amine catalysts allowed the highly enantioselective addition of aldehydes, while using primary amine catalysts led to the enantioselective addition of ketoester nucleophiles. The process was found to be highly regio-, stereo- and enantio-selective and represented the first allene hydrofunctionalization using an synergistic catalysis involving copper

Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction

Synlett ◽  
2021 ◽  
Author(s):  
Loránd Kiss ◽  
Zsanett Benke ◽  
Melinda Nonn ◽  
Attila M. Remete ◽  
Santos Fustero
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Nitrile Oxide ◽  
Amino Acid Derivatives ◽  
Selective Synthesis ◽  
Chemical Transformations ◽  
Bond Functionalization ◽  
Cross Metathesis ◽  
Chlorosulfonyl Isocyanate ◽  
Biological Potential

AbstractThis Account gives an insight into the selective functionalization of some readily available commercial cyclodienes across simple chemical transformations into functionalized small-molecular scaffolds. The syntheses involved selective cycloadditions, followed by ring-opening metathesis (ROM) of the resulting azetidin-2-one derivatives or isoxazoline frameworks and selective cross metathesis (CM) by discrimination of the C=C bonds on the alkenylated heterocycles. The CM protocols have been described when investigated under various conditions with the purpose on exploring chemodifferentiation of the olefin bonds and a study on the access of the corresponding functionalized β-lactam or isoxazoline derivatives is presented. Due to the expanding importance of organofluorine chemistry in drug research as well as of the high biological potential of β-lactam derivatives several illustrative examples to the access of some fluorine-containing molecular entities is also presented in this synopsis.1 Introduction2 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Chlorosulfonyl Isocyanate Cycloaddition3 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Nitrile Oxide Cycloaddition4 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Metathesis5 Functionalization of sSome Cyclodienes across Nitrile Oxide Cycloaddition6 Selective Synthesis of Functionalized Alicycles across Ring-Opening Metathesis7 Selective Synthesis of Functionalized Alicycles through Cross Metathesis8 Summary and Outlook9 List of Abbreviations

Effects of alkoxide alteration on the ring-opening polymerization of ε-caprolactone initiated by n-Bu3SnOR: a DFT study

2014 ◽  
Vol 26 (3) ◽  
pp. 695-703 ◽  
Author(s):  
Chanchai Sattayanon ◽  
Watit Sontising ◽  
Wanich Limwanich ◽  
Puttinan Meepowpan ◽  
Winita Punyodom ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Polymerization ◽  
Dft Study

sp3–sp2vs sp3–sp3C–C Site Selectivity in Rh-Catalyzed Ring Opening of Benzocyclobutenol: A DFT Study

2013 ◽  
Vol 136 (1) ◽  
pp. 169-178 ◽  
Author(s):  
Lina Ding ◽  
Naoki Ishida ◽  
Masahiro Murakami ◽  
Keiji Morokuma
Keyword(s):  
Ring Opening ◽  
Dft Study ◽  
Site Selectivity

Aminkomplexe des Goldes, Teil 9: Gold(I)-halogenid-Komplexe mit primären und azyklischen sekundären Aminen und ihre Oxidation zu Gold(III)-Derivaten

2018 ◽  
Vol 73 (1) ◽  
pp. 43-74 ◽  
Author(s):  
Cindy Döring ◽  
Peter G. Jones
Keyword(s):  
Hydrogen Bonds ◽  
Structure Analysis ◽  
Secondary Amine ◽  
Primary Amine ◽  
Solvent Free ◽  
Secondary Amines ◽  
Primary Amines ◽  
Direct Reaction ◽  
X Ray

AbstractThe reaction of (tht)AuX (X=Cl or Br; tht=tetrahydrothiophene) with various primary amines L leads to products of the form [L2Au]+X−. Packing diagrams of the corresponding structures are dominated by N–H···X hydrogen bonds and (in some cases) aurophilic contacts. The cyclohexylamine derivative was already known as its dichloromethane ⅔-solvate; we have isolated the solvent-free compound and its pentane ¼-solvate, which all show different packing patterns. With acyclic secondary amines, the products are more varied; LAuX and [L2Au]+[AuX2]− were also found. These gold(I) products were generally formed in satisfactory quantities. The attempted oxidation to Au(III) derivatives with PhICl2 or Br2 proved impossible for the primary amine derivatives [although isopropylamine-trichloridogold(III) was obtained unexpectedly from the corresponding cyanide] and unsatisfactory for the secondary amine derivatives. Products LAuX3 and [L2AuX2]+[AuX4]− were identified but were formed in disappointing yields. In isolated cases protonated products (LH)+[AuCl4]−, (LH+)3[AuCl4]−(Cl−)2 or [(Et2N)2CH]+[AuBr4]− were formed, presumably by involvement of the dichloromethane solvent and/or adventitious water. Here also the yields were poor, and some products arose as mixtures. Direct reaction of amines with AuCl3 or (tht)AuX3 was also unsuccessful. All products were characterized by X-ray structure analysis.

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