N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for a-hydroxy, a-chloro, and a-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective a-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under nonoxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.

An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent

PISANI, LAURA;SUPERCHI, Stefano;
2011-01-01

Abstract

N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for a-hydroxy, a-chloro, and a-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective a-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under nonoxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.
2011
File in questo prodotto:
File Dimensione Formato  
Tetrahed_2011_5268.pdf

solo utenti autorizzati

Descrizione: pdf finale
Tipologia: Pdf editoriale
Licenza: DRM non definito
Dimensione 2.02 MB
Formato Adobe PDF
2.02 MB 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/11563/19976
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 17
  • ???jsp.display-item.citation.isi??? 16
social impact