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Synthesis 2023; 55(08): 1285-1297
DOI: 10.1055/a-1975-5291
DOI: 10.1055/a-1975-5291
paper
High-Pressure Activation to Circumvent Product Degradation in the Reaction of Unprotected Glyconitrones with Alkynes
The authors would like to thank the Centre National de la Recherche Scientifique (CNRS) and Univ. Reims Champagne Ardenne (URCA) for financial support. N.N. is grateful to URCA and Ecole Doctorale ABIES for a doctoral allocation.
Abstract
Cycloadditions of nitrones with alkynes usually occur best under heat activation. Due to the instability of the formed isoxazolines, alternative activation methods must be found. Here, hyperbaric conditions are used to transform nitrones generated from unprotected carbohydrates into the corresponding polyhydroxy-isoxazolines at room temperature. The reaction proved completely regioselective in favor of the 5-substituted 4-isoxazolines, and the products are obtained in good yields as mixtures of the two possible diastereoisomers. Further transformations into biologically valuable targets are described. The whole synthesis constitutes a very straightforward procedure for the transformation of aldoses, and is highly compatible with the principles of green chemistry.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1975-5291.
- Supporting Information
Publication History
Received: 07 October 2022
Accepted: 09 November 2022
Accepted Manuscript online:
09 November 2022
Article published online:
15 December 2022
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