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
a  Department of Chemistry and Biology ‘A. Zambelli’, University of Salerno, Via Giovanni Paolo II, 132 84084-Fisciano (SA), Italy   Email: [email protected]
,
Andreas Eitzinger
b  Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria   Email: [email protected]
,
c  Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, 76000 Rouen, France   Email: [email protected]
,
b  Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria   Email: [email protected]
,
a  Department of Chemistry and Biology ‘A. Zambelli’, University of Salerno, Via Giovanni Paolo II, 132 84084-Fisciano (SA), Italy   Email: [email protected]
› Author Affiliations
A.M. wants to thank the Ministero dell’Istruzione, dell’Università e della Ricerca (MIUR) and Università degli Studi di Salerno for financial support. A.E. and M.W. gratefully acknowledge financial support from the Austrian Science Fund (FWF): Project No. P30237. J.F.B. acknowledge that this work has been partially supported by the Institut National des Sciences Appliquées Rouen ( INSA Rouen), Université de Rouen, the Centre National de la Recherche Scientifique (CNRS), European Regional Development Fund, and Labex SynOrg (ANR-11-LABX-0029), and by Region Normandie (CRUNCh network).


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



Publication History

Received: 20 July 2020

Accepted after revision: 22 August 2020

Publication Date:
12 October 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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