Synthesis of New β‐Amino Acid Scaffolds by Means of Ring‐Rearrangement Metathesis
Abstract: The synthesis of some novel functionalized azaheterocyclic β‐amino esters with multiple chiral centers via a stereocontrolled synthetic route has been carried out using some cyclooctene β‐amino acids as starting model compounds. The strategy of the method was planned to create some novel unsaturated N‐protected cyclic β‐amino esters that were subjected to ring‐opening metathesis (ROM) followed by selective ring‐closing metathesis (RCM). A number of experimental conditions were accomplished to investigate the activity of catalysts, yields, conversions, and substrate effect on ring‐rearrangement metathesis (RRM) transformation. Importantly, the procedure used in this synthetic process does not affect the configuration of the chiral centers; therefore, the stereochemistry of the starting cyclooctadiene β‐amino acids predetermined the structure of the new azaheterocyclic derivatives.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Synthesis of New β‐Amino Acid Scaffolds by Means of Ring‐Rearrangement Metathesis ; volume:7 ; number:46 ; year:2022 ; extent:9
ChemistrySelect ; 7, Heft 46 (2022) (gesamt 9)
- Creator
- DOI
-
10.1002/slct.202204244
- URN
-
urn:nbn:de:101:1-2022120914114205292376
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
15.08.2025, 7:23 AM CEST
Data provider
This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Semghouli, Anas
- Remete, Attila M.
- Kiss, Lorand
Other Objects (12)
Selective Transformation of 1,3‐Cyclooctadiene into Novel Functionalized Azaheterocycles, β‐Amino Esters, and Lactams by Means of Ring‐Rearrangement Metathesis
Recent applications of ring-rearrangement metathesis in organic synthesis
Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps
Synthesis of α-Quaternary Amino Esters via Intramolecular Rearrangement
Cyclic Alkyl (amino) Carbene‐Induced Rearrangement of Ga‐Phosphaketene
Olefin Metathesis in Confinement: Towards Covalent Organic Framework Scaffolds for Increased Macrocyclization Selectivity
Sequential Aza-Claisen Rearrangement and Ring-Closing Metathesis as a Route to 1-Benzazepine Derivatives
Synthesis of conformationally restricted amino acids : highly versatile scaffolds
Synthesis of conformationally restricted amino acids : highly versatile scaffolds
Amino-Claisen versus Oxy-Claisen Rearrangement: Regioselective Synthesis of Pyrrolocoumarin Derivatives
The synthesis & derivatisation of amino acids into conformationally restricted unnatural amino acid & spirocyclic scaffolds
Catalytic Decomposition of Long‐Chain Olefins to Propylene via Isomerization‐Metathesis Using Latent Bicyclic (Alkyl)(Amino) Carbene‐Ruthenium Olefin Metathesis Catalysts
Selective Transformation of 1,3‐Cyclooctadiene into Novel Functionalized Azaheterocycles, β‐Amino Esters, and Lactams by Means of Ring‐Rearrangement Metathesis
Recent applications of ring-rearrangement metathesis in organic synthesis
Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps
Synthesis of α-Quaternary Amino Esters via Intramolecular Rearrangement
Cyclic Alkyl (amino) Carbene‐Induced Rearrangement of Ga‐Phosphaketene
Olefin Metathesis in Confinement: Towards Covalent Organic Framework Scaffolds for Increased Macrocyclization Selectivity
Sequential Aza-Claisen Rearrangement and Ring-Closing Metathesis as a Route to 1-Benzazepine Derivatives
Synthesis of conformationally restricted amino acids : highly versatile scaffolds
Synthesis of conformationally restricted amino acids : highly versatile scaffolds
Amino-Claisen versus Oxy-Claisen Rearrangement: Regioselective Synthesis of Pyrrolocoumarin Derivatives
The synthesis & derivatisation of amino acids into conformationally restricted unnatural amino acid & spirocyclic scaffolds
Catalytic Decomposition of Long‐Chain Olefins to Propylene via Isomerization‐Metathesis Using Latent Bicyclic (Alkyl)(Amino) Carbene‐Ruthenium Olefin Metathesis Catalysts
Selective Transformation of 1,3‐Cyclooctadiene into Novel Functionalized Azaheterocycles, β‐Amino Esters, and Lactams by Means of Ring‐Rearrangement Metathesis
Recent applications of ring-rearrangement metathesis in organic synthesis
Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps
Synthesis of α-Quaternary Amino Esters via Intramolecular Rearrangement
Cyclic Alkyl (amino) Carbene‐Induced Rearrangement of Ga‐Phosphaketene
Olefin Metathesis in Confinement: Towards Covalent Organic Framework Scaffolds for Increased Macrocyclization Selectivity
Sequential Aza-Claisen Rearrangement and Ring-Closing Metathesis as a Route to 1-Benzazepine Derivatives
Synthesis of conformationally restricted amino acids : highly versatile scaffolds
Synthesis of conformationally restricted amino acids : highly versatile scaffolds
Amino-Claisen versus Oxy-Claisen Rearrangement: Regioselective Synthesis of Pyrrolocoumarin Derivatives
The synthesis & derivatisation of amino acids into conformationally restricted unnatural amino acid & spirocyclic scaffolds