Rearrangement of 3-Hydroxyazetidines into 2-Oxazolines

    • Ian R. Baxendale1
    • Michele Ruggeri1
    • Amanda W. Dombrowski2
    • Stevan W. Djuric3
    • 1Department of Chemistry, University of Durham, Durham DH1 3LE, United Kingdom
    • 2 Discovery Chemistry and Technology AbbVie Inc., North Chicago, Illinois 60064, United States
    • 3Discovery Chemistry and Technology Consulting LLC, New Bern, North Carolina 28562, United States

    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 cyclization leading to a new class of macrocycle. The final cyclization 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.

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