Regioselective Base-Promoted Nucleophilic Ring Opening of Spirocyclic 2,6-Dioxopiperazines: Synthesis ofN-(1-Carboxycyclohexyl)amino Acid Derivatives

2007 ◽  
Vol 2007 (3) ◽  
pp. 548-554 ◽  
Author(s):  
Juan A. González-Vera ◽  
M. Teresa García-López ◽  
Rosario Herranz
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Amino Acid Derivatives ◽  
Nucleophilic Ring Opening

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

Living Ring-Opening Metathesis Polymerization of Enantiopure Norbornene-type β-Amino Acid Derivatives

Synlett ◽  
2001 ◽  
Vol 2001 (12) ◽  
pp. 1875-1877 ◽  
Author(s):  
Carsten Bolm ◽  
Christian L. Dinter ◽  
Ingo Schiffers ◽  
Laurent Defrère
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Amino Acid Derivatives ◽  
Ring Opening Metathesis Polymerization ◽  
Metathesis Polymerization
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