Copper‐Catalyzed A 3 ‐Coupling for the Diversity‐Oriented Synthesis of Proline‐Derived Alkynyl‐Substituted Peptidomimetic Scaffolds

The Aldehyde–Amine–Alkyne reaction (A 3 ) proves to be a powerful methodology as a coupling step of the Build/Couple/Pair approach in Diversity Oriented Synthesis (DOS) because it can lead to the formation of polyfunctionalized intermediates suitable for the creation of different molecular entities....

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Veröffentlicht in:European journal of organic chemistry 2019-09, Vol.2019 (36), p.6203-6210
Hauptverfasser: Innocenti, Riccardo, Lenci, Elena, Baldini, Lorenzo, Faggi, Cristina, Menchi, Gloria, Trabocchi, Andrea
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Sprache:eng
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Zusammenfassung:The Aldehyde–Amine–Alkyne reaction (A 3 ) proves to be a powerful methodology as a coupling step of the Build/Couple/Pair approach in Diversity Oriented Synthesis (DOS) because it can lead to the formation of polyfunctionalized intermediates suitable for the creation of different molecular entities. In this work we used cyclic α‐amino aldehyde moieties for the microwave‐assisted A 3 coupling reaction, resulting in the generation of the corresponding propargylamines and successively exploited in intramolecular pairing reactions to obtain a pool of different alkynyl‐substituted peptidomimetic compounds.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900703