The preparation of new chiral amino alcohols that possess a flexible biphenylazepine moiety and can work as tropos catalysts, is presented. In these compounds, the sign of the induced axial chirality depends on the nature of stereogenic centers near the flexible fragment and can determine the stereochemical outcome in asymmetric reactions mediated by them. The efficiency of these new ligands has been explored in the asymmetric addition of arylzinc species prepared in situ to aromatic aldehydes. Among them, amino alcohol (1R,2S)-4 gave the best results and afforded optically active diarymethanols, which are precursors of well-known chiral drugs, in high yields and with enantioselectivity up to 96%.

Tropos Aminoalcohol Mediated Enantioselective Aryl Transfer Reactions to Aromatic Aldehydes

PISANI, LAURA;SUPERCHI, Stefano;SCAFATO, Patrizia
2014-01-01

Abstract

The preparation of new chiral amino alcohols that possess a flexible biphenylazepine moiety and can work as tropos catalysts, is presented. In these compounds, the sign of the induced axial chirality depends on the nature of stereogenic centers near the flexible fragment and can determine the stereochemical outcome in asymmetric reactions mediated by them. The efficiency of these new ligands has been explored in the asymmetric addition of arylzinc species prepared in situ to aromatic aldehydes. Among them, amino alcohol (1R,2S)-4 gave the best results and afforded optically active diarymethanols, which are precursors of well-known chiral drugs, in high yields and with enantioselectivity up to 96%.
2014
File in questo prodotto:
File Dimensione Formato  
EurJOC_2014_5939.pdf

solo utenti autorizzati

Descrizione: pdf finale
Tipologia: Pdf editoriale
Licenza: DRM non definito
Dimensione 381.57 kB
Formato Adobe PDF
381.57 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/11563/89494
 Attenzione

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

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 18
  • ???jsp.display-item.citation.isi??? 16
social impact