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