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.
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9710
9717
Lenci, Elena; Rossi, Alessio; Menchi, Gloria; Trabocchi, Andrea
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2158/1103029
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