A mild approach to synthesise enantiopure glycine-derived 5-phenylthiomorpholinone

Monir, D. K. ORCID: https://orcid.org/0000-0001-9511-063X and Harwood, L. M. ORCID: https://orcid.org/0000-0002-8442-7380 (2021) A mild approach to synthesise enantiopure glycine-derived 5-phenylthiomorpholinone. Tetrahedron, 84. 132035. ISSN 0040-4020 doi: 10.1016/j.tet.2021.132035

Abstract/Summary

A seven-step synthetic route has been developed to access the labile C-3 unsubstituted 5-phenylthiomorpholinone system for the first time. The key step involved the nucleophilic ring opening of Boc-phenylmorpholinone to give the corresponding methyl ester. The sulfur introduction was accomplished through a Mitsunobu reaction to yield a thioacetate, which was then hydrolysed to provide the thiol acid. Cyclization of the thiol acid was achieved using DCC in the presence of DMAP, to give Boc-phenylthiomorpholinone and subsequent deprotection afforded the elusive C-3 unsubstituted 5-phenylthiomorpholinone.

Item Type	Article
URI	https://centaur.reading.ac.uk/id/eprint/98350
Identification Number/DOI	10.1016/j.tet.2021.132035
Refereed	Yes
Divisions	Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Publisher	Elsevier
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