Synthesis
DOI: 10.1055/s-0036-1590924
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Isoxazolidinyl Epoxides by Oxone Treatment of 2,3-Dihydroisoxazoles in Acetone–Water Solution: A New Stereoselective Approach to Hydroxy-Substituted Isoxazolidines

Ondrej Záborskýa, Radka Štadániováa, Jana Doháňošováb, Ján Moncolc, Róbert Fischer*a
  • aInstitute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 81237 Bratislava, Slovak Republic   Email: robert.fischer@stuba.sk
  • bCentral Laboratories, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic
  • cInstitute of Inorganic Chemistry, Technology and Materials, Slovak University of Technology in Bratislava, Radlinského 9, 81237 Bratislava, Slovak Republic
This work was supported by the Slovak Grant Agencies APVV, Bratislava (project no. APVV-14-0147), VEGA, Bratislava (project no. 1/0488/14), and ASFEU, Bratislava (ITMS project No. 26240120001 and 26240120025). This article was created with the support of the ­MŠVVaŠ of the Slovak Republic within the Research and Development ­Operational Programme for the project ‘University Science Park of STU Bratislava’ (ITMS project No. 26240220084) co-funded by the ­European Regional Development Fund.
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Publication History

Received: 27 July 2017

Accepted after revision: 12 September 2017

Publication Date:
27 September 2017 (eFirst)

Abstract

A practical and efficient synthesis of new class of isoxazoli­dinyl epoxides by direct treatment of 4,5-unsubstituted 2,3-dihydroisoxazoles with Oxone and NaHCO3 in acetone/water solution is described. All epoxidation reactions proceed with excellent anti-selectivity and provide stable products in very good yields. A concept for the development of stereoselective approach to 3,4-trans-hydroxy-substituted isoxazolidines, namely triazole derivatives as important molecules in medicinal chemistry is presented. The synthesis is characterized by highly syn-stereoselective conversion of epoxides to anomeric bromoisoxazolidines, which are found to be powerful reaction intermediates for the coupling reactions with various nucleophiles.

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