We first report that highly polarized organometallic compounds of s-block elements add smoothly to chiral N-tertbutanesulfinyl imines in the biodegradable D-sorbitol/choline chloride eutectic mixture, thereby granting access to enantioenriched primary amines after quantitatively deblocking the sulfinyl group. The practicability of the methodology was further highlighted by (a) working at ambient temperature and under air, (b) very short reaction times (2 min), (c) the preparation of diastereomeric sulfinamides in very good yields (74–98%) and with a broad substrate scope, (d) the possibility of scaling up the process, and (e) the asymmetric synthesis of both the chiral amine side-chain of (R,R)-Formoterol (96% ee) and the pharmaceutically relevant (R)-Cinacalcet (98% ee).

Addition of Highly Polarized Organometallic Compounds to N-tert-Butanesulfinyl Imines in Deep Eutectic Solvents under Air: Preparation of Chiral Amines of Pharmaceutical Interest

Luciana Cicco;Antonio Salomone;Paola Vitale;Filippo M. Perna
;
Vito Capriati
2020-01-01

Abstract

We first report that highly polarized organometallic compounds of s-block elements add smoothly to chiral N-tertbutanesulfinyl imines in the biodegradable D-sorbitol/choline chloride eutectic mixture, thereby granting access to enantioenriched primary amines after quantitatively deblocking the sulfinyl group. The practicability of the methodology was further highlighted by (a) working at ambient temperature and under air, (b) very short reaction times (2 min), (c) the preparation of diastereomeric sulfinamides in very good yields (74–98%) and with a broad substrate scope, (d) the possibility of scaling up the process, and (e) the asymmetric synthesis of both the chiral amine side-chain of (R,R)-Formoterol (96% ee) and the pharmaceutically relevant (R)-Cinacalcet (98% ee).
File in questo prodotto:
File Dimensione Formato  
2020_CSC_accepted.pdf

non disponibili

Tipologia: Documento in Versione Editoriale
Licenza: NON PUBBLICO - Accesso privato/ristretto
Dimensione 1.26 MB
Formato Adobe PDF
1.26 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/11586/294051
Citazioni
  • ???jsp.display-item.citation.pmc??? 9
  • Scopus 37
  • ???jsp.display-item.citation.isi??? 35
social impact