Rearrangement of 3-Hydroxyazetidines into 2-Oxazolines
Michele Ruggeri, Amanda W. Dombrowski, Stevan W. Djurić, Ian R. Baxendale
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 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.
Topics & Concepts
ChemistryIntramolecular forceTransformation (genetics)Combinatorial chemistryIntramolecular reactionCascade reactionSubstrate (aquarium)Sequence (biology)CascadeStereochemistryOrganic chemistryCatalysisGeologyChromatographyBiochemistryOceanographyGeneSynthesis and Catalytic ReactionsSynthesis of β-Lactam CompoundsChemical Synthesis and Analysis