scholarly journals Front Cover: Stereocontrolled Synthesis of Fluorine-Containing Piperidine γ-Amino Acid Derivatives (Eur. J. Org. Chem. 12/2019)

2019 ◽  
Vol 2019 (12) ◽  
pp. 2176-2176
Author(s):  
Lamiaa Ouchakour ◽  
Renáta A. Ábrahámi ◽  
Enikő Forró ◽  
Matti Haukka ◽  
Ferenc Fülöp ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Front Cover ◽  
Stereocontrolled Synthesis

scholarly journals Stereocontrolled Synthesis of Fluorine-Containing Piperidine γ-Amino Acid Derivatives

2018 ◽  
Vol 2019 (12) ◽  
pp. 2202-2211 ◽  
Author(s):  
Lamiaa Ouchakour ◽  
Renáta A. Ábrahámi ◽  
Enikő Forró ◽  
Matti Haukka ◽  
Ferenc Fülöp ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Stereocontrolled Synthesis

From nature, through chemical synthesis, toward use in agriculture: Oryzoxymycin case study

2009 ◽  
Vol 81 (1) ◽  
pp. 105-112 ◽  
Author(s):  
Regina N. Bwire ◽  
Runner R. Majinda ◽  
Ishmael B. Masesane ◽  
Patrick G. Steel
Keyword(s):  
Amino Acid ◽  
Organic Acids ◽  
Hydrogenation Reaction ◽  
Diels Alder ◽  
Transfer Hydrogenation ◽  
Amino Acid Derivatives ◽  
Oxidation Reactions ◽  
Stereocontrolled Synthesis ◽  
Transfer Hydrogenation Reaction

The Diels-Alder adducts of ethyl (E)-3-nitroacrylate and furan provided a common and versatile template for the stereocontrolled synthesis of an isomer of the natural product oryzoxymycin and polyhydroxylated cyclohexyl β-amino acid derivatives. The strategy for the synthesis of the polyhydroxylated cyclic β-amino acid derivatives involved base-induced fragmentation of the oxanorbornene skeleton and face selective oxidation reactions. A Pd-catalyzed transfer hydrogenation reaction in the presence of organic acids is also described. This reaction is amenable to being enantioselective through use of optical pure chiral organic acids.

scholarly journals Application of Metathesis Reactions in the Synthesis and Transformations of Functionalized β-Amino Acid Derivatives

Synthesis ◽  
2018 ◽  
Vol 50 (18) ◽  
pp. 3571-3588 ◽  
Author(s):  
Loránd Kiss ◽  
Márton Kardos ◽  
Csaba Vass ◽  
Ferenc Fülöp
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Ring Opening ◽  
Amino Acid Derivatives ◽  
Ring Closing Metathesis ◽  
Ring Systems ◽  
Bond Functionalization ◽  
Cross Metathesis ◽  
Stereocontrolled Synthesis ◽  
Metathesis Reactions

Because of their biological relevance, cyclic β-amino acids have generated increasing interest and had significant impact in drug research over the past two decades. Their preparation and further functionalization towards new types of molecular entities have received large interest in synthetic and medicinal chemistry. Various types of metathesis reactions, such as ring-opening (ROM), ring-closing (RCM), or cross metathesis (CM) are used widely for access to either alicyclic β-amino acids or other densely functionalized derivatives of this group of compounds. This account intends to provide an insight into the most relevant synthetic routes to this class of derivatives with the application of metathesis reactions. The review focuses on the presentation of selective and stereocontrolled methodologies in view of versatility, robustness, limitations and efficiency.1 Introduction2 Synthesis and Transformation of Cyclic β-Amino Acids through Metathesis Reactions2.1 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Ring-Closing Metathesis2.2 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Cross Metathesis2.3 Synthesis of β-Amino Acids with Larger Ring Systems by Ring- Closing Metathesis2.4 Synthesis of β-Amino Acids with Condensed Ring Systems by Ring-Rearrangement Metathesis2.5 Stereocontrolled One-Step Synthesis of Functionalized Cispentacin and Transpentacin Derivatives2.5.1 Stereocontrolled Synthesis of Functionalized Cispentacin and Transpentacin Derivatives through Ring-Opening Metathesis of Norbornene β-Amino Acid Derivatives2.5.2 Stereocontrolled Synthesis of Functionalized Azetidinones and β-Amino Acid Derivatives from Condensed Ring β-Lactams by Ring-Opening Metathesis2.5.3 Carbon–Carbon Double Bond Functionalization of β-Amino Acid Derivatives and β-Lactams with α,β-Unsaturated Carbonyl Compounds through Cross Metathesis2.5.4 Synthesis of Functionalized β-Amino Acid Derivatives and β-Lactams through Chemoselective Cross Metathesis3 Conclusions and Outlook

Diversity-Oriented Stereocontrolled Synthesis of Some Piperidine- and Azepane-Based Fluorine-Containing β-Amino Acid Derivatives

Synthesis ◽  
2020 ◽  
Author(s):  
Loránd Kiss ◽  
Melinda Nonn ◽  
Dominika Kara ◽  
Lamiaa Ouchakour ◽  
Enikő Forró ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Reductive Amination ◽  
Structural Diversity ◽  
Ring Cleavage ◽  
Amino Acid Derivatives ◽  
Diversity Oriented Synthesis ◽  
Conformationally Restricted ◽  
Selective Functionalization ◽  
Stereocontrolled Synthesis

AbstractStructural diversity-oriented synthesis of some azaheterocyclic β-amino acid derivatives has been accomplished by selective functionalization of readily available cyclodienes. The stereocontrolled synthetic concept was based on the oxidative ring cleavage of unsaturated cyclic β-amino acids derived from cycloalkadiene, followed by ring closing with double reductive amination, which furnished some conformationally restricted β-amino acid derivatives with a piperidine or azepane core.

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