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

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• 作者：Abderrahman El Bouakher ; Ronan Le Goff ; Jordan Tasserie ; Jérôme Lhoste ; Arnaud Martel ; Sébastien Comesse
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：18
• 期：10
• 页码：2383-2386
• 全文大小：348K
• 年卷期：0
• ISSN：1523-7052

文摘

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.