A rearrangement of 3-hydroxyazetidines into 2-oxazolines

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

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