Issue 45, 2017

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

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.

Graphical abstract: Short synthesis of polyfunctional sp3-rich threonine-derived morpholine scaffolds

Supplementary files

Article information

Article type
Paper
Submitted
03 Oct 2017
Accepted
03 Nov 2017
First published
06 Nov 2017

Org. Biomol. Chem., 2017,15, 9710-9717

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

E. Lenci, A. Rossi, G. Menchi and A. Trabocchi, Org. Biomol. Chem., 2017, 15, 9710 DOI: 10.1039/C7OB02454A

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