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

Antonio Macchia; Andreas Eitzinger; Jean-François Brière; Mario Waser; Antonio Massa

doi:10.1055/s-0040-1706483

Synthesis, Table of Contents

Synthesis 2021; 53(01): 107-122
DOI: 10.1055/s-0040-1706483

short review

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

Antonio Macchia

^aDepartment of Chemistry and Biology ‘A. Zambelli’, University of Salerno, Via Giovanni Paolo II, 132 84084-Fisciano (SA), Italy Email: amassa@unisa.it

,

Andreas Eitzinger

^bInstitute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria Email: mario.waser@jku.at

,

Jean-François Brière ∗

^cNormandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, 76000 Rouen, France Email: jean-francois.briere@insa-rouen.fr

,

Mario Waser ∗

^bInstitute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria Email: mario.waser@jku.at

,

Antonio Massa ∗

^aDepartment of Chemistry and Biology ‘A. Zambelli’, University of Salerno, Via Giovanni Paolo II, 132 84084-Fisciano (SA), Italy Email: amassa@unisa.it

› Author Affiliations

Abstract

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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 recently been successfully employed for this task and some of the most promising approaches will be discussed.

1 Introduction

2 Isoxazol-5-ones as Nucleophiles

2.1 Isoxazol-5-ones as C-Nucleophiles

2.2 Isoxazol-5-ones as N-Nucleophiles

2.3 Isoxazol-5-ones as C-Nucleophiles in Cyclization Processes

3 Asymmetric Construction of Isoxazolidin-5-ones

3.1 Enantioselective α-Functionalizations of Isoxazolidin-5-ones

4 Arylideneisoxazol-5-ones in Conjugated Addition

5 Conclusions

Key words

asymmetric catalysis - organocatalysis - metal catalysts - heterocycles - chiral building blocks

Full Text

References

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