CINECA IRIS Institutional Research Information System
IRIS è la soluzione IT che facilita la raccolta e la gestione dei dati relativi alle attività e ai prodotti della ricerca. Fornisce a ricercatori, amministratori e valutatori gli strumenti per monitorare i risultati della ricerca, aumentarne la visibilità e allocare in modo efficace le risorse disponibili.
EnglishA straightforward and fully stereoselective synthesis of a new class of peptidomimetics, that is alpha-oxo-gamma-acylaminoamides, was achieved starting from various benzaldehydes by a sequence of 1) an asymmetric organocatalytic Mannich reaction, 2) a Passerini multicomponent reaction, 3) an amine deprotection–acyl migration protocol, and 4) a final oxidation. The whole sequence can be performed without purification of the intermediates and represents the first example of a homo-Passerini– amine deprotection–acyl migration (PADAM) strategy. Highly stereoselective reduction of the alpha-oxo-gamma-acylaminoamides afforded alpha-hydroxy-gamma-acylaminoamides as well. In some cases both diastereomers were obtained by simply changing the reducing agent. Finally, starting from protected salicylaldehyde, the same sequence, followed by a Mitsunobu cyclization, afforded highly substituted chromanes.
Scheda prodotto non validato
Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo
| Titolo: | The homo-PADAM Protocol: Stereoselective and Operationally Simple Synthesis of alpha-Oxo or alpha-Hydroxy-gamma-acylaminoamides and Chromanes |
| Autori: | |
| Data di pubblicazione: | 2013 |
| Rivista: | |
| Abstract: | A straightforward and fully stereoselective synthesis of a new class of peptidomimetics, that is alpha-oxo-gamma-acylaminoamides, was achieved starting from various benzaldehydes by a sequence of 1) an asymmetric organocatalytic Mannich reaction, 2) a Passerini multicomponent reaction, 3) an amine deprotection–acyl migration protocol, and 4) a final oxidation. The whole sequence can be performed without purification of the intermediates and represents the first example of a homo-Passerini– amine deprotection–acyl migration (PADAM) strategy. Highly stereoselective reduction of the alpha-oxo-gamma-acylaminoamides afforded alpha-hydroxy-gamma-acylaminoamides as well. In some cases both diastereomers were obtained by simply changing the reducing agent. Finally, starting from protected salicylaldehyde, the same sequence, followed by a Mitsunobu cyclization, afforded highly substituted chromanes. |
| Handle: | http://hdl.handle.net/11567/631175 |
| Appare nelle tipologie: | 01.01 - Articolo su rivista |
File in questo prodotto:
http://hdl.handle.net/11567/631175
Copyright © 2021