An asymmetric synthesis of α-aryl amino-β-nitro cyclohexanes has been achieved by means of a tandem aza-Michael addition-protonation reaction starting from 1-nitro cyclohexene and anilines. The transformation is proposed to proceed via a transient nitrile enolate which is subsequently stereoselectively protonated by an intramolecular transfer of the proton from nitrogen to the nitronate α-carbon.
Stereoselective aza-Michael addition of anilines to 1-nitro cyclohexene by intramolecular protonation
GHISU, LORENZA;MELIS, NICOLA;SECCI, FRANCESCO;FRONGIA, ANGELO
2015-01-01
Abstract
An asymmetric synthesis of α-aryl amino-β-nitro cyclohexanes has been achieved by means of a tandem aza-Michael addition-protonation reaction starting from 1-nitro cyclohexene and anilines. The transformation is proposed to proceed via a transient nitrile enolate which is subsequently stereoselectively protonated by an intramolecular transfer of the proton from nitrogen to the nitronate α-carbon.
File in questo prodotto:
| File | Dimensione | Formato | |
|---|---|---|---|
|
Tetraedron Lett 2015.pdf
Solo gestori archivio
Tipologia:
versione editoriale (VoR)
Dimensione
586.4 kB
Formato
Adobe PDF
|
586.4 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I metadati presenti in IRIS UNICA sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono protetti da diritto d'autore, salvo diversa indicazione.
