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

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
Dimensione 586.4 kB
Formato Adobe PDF
586.4 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11584/189004
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 2
social impact