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Synthesis of Oxazolidin-4-ones: Domino O‑Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation

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posted on 29.04.2016, 13:29 by Abderrahman El Bouakher, Ronan Le Goff, Jordan Tasserie, Jérôme Lhoste, Arnaud Martel, Sébastien Comesse
An original and rapid domino reaction for access to oxazolidin-4-ones is presented. Simply by heating α-bromoamido alcohol in the presence of KNaCO3 and water with readily prepared Michael acceptors, an unprecedented molecular rearrangement is generated. This new methodology enables the hitherto unreported synthesis of functionalized oxazolidin-4-ones. The process was proved to be compatible with a wide variety of substrates, and high regioselectivities were achieved.