Asymmetric Synthesis of Isoxazol-5-ones and Isoxazolidin-5-ones - Normandie Université Access content directly
Journal Articles Synthesis: Journal of Synthetic Organic Chemistry Year : 2021

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

Antonio Macchia
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Andreas Eitzinger
  • Function : Author
Mario Waser
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  • PersonId : 1084118
Antonio Massa
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  • PersonId : 1084119


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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Dates and versions

hal-03037370 , version 1 (03-12-2020)



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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