A convenient synthesis of novel complex morpholines was achieved by a two-step process involving a Petasis three-component coupling reaction of glycolaldehyde, organoboronic acid and different amines, followed by an acid- or base-mediated intramolecular cyclization. The use of threonine derivatives with glycolaldehyde in the Petasis reaction has been studied and successfully applied in the process, achieving morpholines with a higher fraction of sp3 carbon atoms compared to blockbuster drugs.

Short synthesis of polyfunctional sp3-rich threonine-derived morpholine scaffolds / Lenci, Elena; Rossi, Alessio; Menchi, Gloria; Trabocchi, Andrea. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 15:(2017), pp. 9710-9717. [10.1039/C7OB02454A]

Short synthesis of polyfunctional sp3-rich threonine-derived morpholine scaffolds

Lenci, Elena;Menchi, Gloria;Trabocchi, Andrea
2017

Abstract

A convenient synthesis of novel complex morpholines was achieved by a two-step process involving a Petasis three-component coupling reaction of glycolaldehyde, organoboronic acid and different amines, followed by an acid- or base-mediated intramolecular cyclization. The use of threonine derivatives with glycolaldehyde in the Petasis reaction has been studied and successfully applied in the process, achieving morpholines with a higher fraction of sp3 carbon atoms compared to blockbuster drugs.
2017
15
9710
9717
Lenci, Elena; Rossi, Alessio; Menchi, Gloria; Trabocchi, Andrea
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1103029
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 17
  • ???jsp.display-item.citation.isi??? 16
social impact