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

• DOI: 10.1021/acs.orglett.6b00851
• Publication Date: 2016-04-29T13:32:29Z
• Authors: Abderrahman El Bo...; Ronan Le Goff; Jordan Tasserie; Jérôme Lhoste; Arnaud Martel; Sébastien Comesse
• Keywords: Domino; Michael reaction

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 water with readily prepared Michael acceptors, an unprecedented molecular rearrangement generated. This new methodology enables hitherto unreported synthesis functionalized oxazolidin-4-ones. The process was proved be compatible a wide variety substrates, high regioselectivities were achieved.