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Synthesis 2025; 57(06): 1213-1222
DOI: 10.1055/a-2503-2981
DOI: 10.1055/a-2503-2981
paper
Zinc-Mediated Diastereoselective Acyloxyallylation of Isoxazolidine-4,5-diols
Authors
This work was supported by the Vedecká grantová agentúra MŠVVaŠ of the Slovak Republic (Slovak Grant Agency for Science VEGA, Project no. 1/0152/23) and Agentúra na podporu výskumu a vývoja (APVV, Project no. APVV-2023-0006). The authors gratefully acknowledge the financial support of Výskumná a inovačná autorita, Research and Innovation Authority, ‘Large Project for Excellent Researchers’ (VAIA, Project No. 09I03-03-V03-00029).
Abstract
The synthesis of new N-Boc- and N-Cbz-protected δ-(hydroxyamino)-α,β,γ-triols is described for the first time. Products were prepared from 3,4-trans-isoxazolidine-4,5-diols, containing different substituents at the C-3 position, by a zinc-mediated acyloxyallylation reaction in good to excellent yields with excellent 3,4-anti simple diastereoselectivity and good 4,5-syn facial diastereoselectivity. Reductive cleavage of the N–O bond can provide δ-amino-α,β,γ-triol, thus demonstrating the potential synthetic utility of δ-(hydroxyamino)-α,β,γ-triols as useful building blocks for bioactive molecules.
Key words
isoxazolidine-4,5-diols - acyloxyallylation - (hydroxyamino)triols - diastereoselectivity - crystal structuresSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2503-2981.
- Supporting Information (PDF)
- CIF File (ZIP)
Publication History
Received: 30 September 2024
Accepted after revision: 16 December 2024
Accepted Manuscript online:
16 December 2024
Article published online:
05 February 2025
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