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

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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

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Publication details

The article was received on 03 Oct 2017, accepted on 03 Nov 2017 and first published on 06 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02454A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Short synthesis of polyfunctional sp3-rich threonine-derived morpholine scaffolds

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

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