Chemodiscrimination of Olefin Bonds Through Cross-Metathesis Reactions - Synthesis of Functionalized β-Lactam and β-Amino Acid Derivatives

2019 ◽  
Vol 2019 (31-32) ◽  
pp. 5285-5293 ◽  
Author(s):  
Melinda Nonn ◽  
Zsanett Benke ◽  
Santos Fustero ◽  
Ferenc Fülöp ◽  
Loránd Kiss
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Cross Metathesis ◽  
Metathesis Reactions

Olefin-Bond Chemodifferentiation through Cross-Metathesis Reactions: A Stereocontrolled Approach to Functionalized β2,3 -Amino Acid Derivatives

2017 ◽  
Vol 2017 (14) ◽  
pp. 1894-1901 ◽  
Author(s):  
Márton Kardos ◽  
Loránd Kiss ◽  
Matti Haukka ◽  
Santos Fustero ◽  
Ferenc Fülöp
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Cross Metathesis ◽  
Metathesis Reactions

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 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

scholarly journals An Efficient Enantioselective Approach to Cyclic β-Amino Acid Derivatives via Olefin Metathesis Reactions.

ChemInform ◽  
2006 ◽  
Vol 37 (37) ◽  
Author(s):  
Giordano Lesma ◽  
Bruno Danieli ◽  
Alessandro Sacchetti ◽  
Alessandra Silvani
Keyword(s):  
Amino Acid ◽  
Olefin Metathesis ◽  
Amino Acid Derivatives ◽  
Metathesis Reactions

Asymmetric Synthesis of Fluorinated Cyclic β-Amino Acid Derivatives through Cross Metathesis

2006 ◽  
Vol 8 (20) ◽  
pp. 4633-4636 ◽  
Author(s):  
Santos Fustero ◽  
María Sánchez-Roselló ◽  
Juan F. Sanz-Cervera ◽  
José Luis Aceña ◽  
Carlos del Pozo ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
Cross Metathesis

scholarly journals Microwave-Accelerated Cross-Metathesis Reactions of N-Allyl Amino Acid Substrates.

ChemInform ◽  
2006 ◽  
Vol 37 (5) ◽  
Author(s):  
Sally-Ann Poulsen ◽  
Laurent F. Bornaghi
Keyword(s):  
Amino Acid ◽  
Cross Metathesis ◽  
Metathesis Reactions

scholarly journals Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates

2005 ◽  
Vol 46 (43) ◽  
pp. 7389-7392 ◽  
Author(s):  
Sally-Ann Poulsen ◽  
Laurent F. Bornaghi
Keyword(s):  
Amino Acid ◽  
Cross Metathesis ◽  
Metathesis Reactions
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