A rearrangement of 3-hydroxyazetidines into 2-oxazolines

Ruggeri, Michele; Dombrowski, Amanda W; Djuric, Stevan W; Baxendale, Ian R.

doi:10.1021/acs.joc.0c00656

A rearrangement of 3-hydroxyazetidines into 2-oxazolines

Ruggeri, Michele; Dombrowski, Amanda W; Djuric, Stevan W; Baxendale, Ian R.

Authors

Michele Ruggeri

Amanda W Dombrowski

Stevan W Djuric

Professor Ian Baxendale i.r.baxendale@durham.ac.uk
Professor

Abstract

A novel rearrangement sequence of 3-hydroxyazetidines via a Ritter initiated cascade provides highly substituted 2-oxazolines in high yields. The reaction conditions and substrate scope of the transformation have been studied demonstrating the generality of the process. The derived products can also be functionalized in order to undergo further intramolecular cyclisation leading to a new class of macrocycle. The final cyclisation step was shown to be a transformation amenable to continuous flow processing allowing for a dramatic reduction in the reaction time and simple scale-up.

Citation

Ruggeri, M., Dombrowski, A. W., Djuric, S. W., & Baxendale, I. R. (2020). A rearrangement of 3-hydroxyazetidines into 2-oxazolines. Journal of Organic Chemistry, 85(11), 7276-7286. https://doi.org/10.1021/acs.joc.0c00656

Journal Article Type	Article
Online Publication Date	May 5, 2020
Publication Date	Jun 5, 2020
Deposit Date	May 6, 2020
Publicly Available Date	May 5, 2021
Journal	Journal of Organic Chemistry
Print ISSN	0022-3263
Electronic ISSN	1520-6904
Publisher	American Chemical Society
Peer Reviewed	Peer Reviewed
Volume	85
Issue	11
Pages	7276-7286
DOI	https://doi.org/10.1021/acs.joc.0c00656

Files

Accepted Journal Article (392 Kb)
PDF

Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.0c00656