Synthesis of 3,5-disubstituted isoxazoles through a 1,3-dipolar cycloaddition reaction between alkynes and nitrile oxides generated from O-silylated hydroxamic acids

Carloni, Laure-Elie, Mohnani, Stefan and Bonifazi, Davide ORCID: https://orcid.org/0000-0001-5717-0121 2019. Synthesis of 3,5-disubstituted isoxazoles through a 1,3-dipolar cycloaddition reaction between alkynes and nitrile oxides generated from O-silylated hydroxamic acids. European Journal of Organic Chemistry 2019 (44) , pp. 7322-7334. 10.1002/ejoc.201901045

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Abstract

In this paper, we report the regioselective synthesis of 3,5‐disubstituted isoxazoles by 1,3‐dipolar cycloaddition between alkynyl dipolarophiles and nitrile oxide dipoles generated in‐situ from O‐silylated hydroxamic acids in the presence of trifluoromethanesulfonic anhydride and NEt3. Thanks to the mild, metal‐free and oxidant‐free conditions that this strategy offers, the reaction was successfully applied to a wide variety of alkynyl dipolarophiles, demonstrating the tolerance of this approach to diverse functional groups. In particular, we have shown that the method was compatible with biological molecules such as peptides and peptide nucleic acids (PNA). This protocol constitutes another example of metal‐free 1,3‐dipolar cycloaddition leading to the regioselective formation of isoxazoles.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	1434-193X
Funders:	European Research Council
Date of First Compliant Deposit:	1 October 2019
Date of Acceptance:	26 August 2019
Last Modified:	12 Nov 2024 19:15
URI:	https://orca.cardiff.ac.uk/id/eprint/125818

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