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A rearrangement of 3-hydroxyazetidines into 2-oxazolines

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

A rearrangement of 3-hydroxyazetidines into 2-oxazolines Thumbnail


Authors

Michele Ruggeri

Amanda W Dombrowski

Stevan W Djuric



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.

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
Public URL https://durham-repository.worktribe.com/output/1271450

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Accepted Journal Article (392 Kb)
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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





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