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Asymmetric Synthesis of Isoxazol-5-ones and Isoxazolidin-5-ones

Abstract : Isoxazol-5-ones and isoxazolidin-5-ones represent two important classes of heterocycles, with several applications as bioactive compounds and as versatile building blocks for further transformations. Unlike the parent aromatic isoxazoles, the presence of one or two stereocenters in the ring renders their asymmetric construction particularly important. In this review, starting from the description of general features and differences between these two related compound families, we present an overview on the most important enantioselective synthesis strategies to access these heterocycles. Both, chiral metal catalysts and organocatalysts, have been successfully employed for this task in the last years and some of the most promising approaches will be discussed herein. 1) Introduction 2) Isoxazol-5-ones as nucleophiles 3) Asymmetric construction of isoxazolidin-5-ones 4) Arylideneisoxazol-5-ones in conjugated addition 5) Conclusions
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Contributor : Jean-François Brière Connect in order to contact the contributor
Submitted on : Thursday, December 3, 2020 - 9:37:45 AM
Last modification on : Tuesday, September 27, 2022 - 4:33:09 AM
Long-term archiving on: : Thursday, March 4, 2021 - 6:34:24 PM


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Antonio Macchia, Andreas Eitzinger, Jean-François Brière, Mario Waser, Antonio Massa. Asymmetric Synthesis of Isoxazol-5-ones and Isoxazolidin-5-ones. Synthesis: Journal of Synthetic Organic Chemistry, 2021, 53 (1), pp.107-122. ⟨10.1055/s-0040-1706483⟩. ⟨hal-03037370⟩



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