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Synthesis
DOI: 10.1055/a-2503-2981
paper

Zinc-Mediated Diastereoselective Acyloxyallylation of Isoxazolidine-4,5-diols

Lukáš Ďurina 
1   Department of Organic Chemistry, Slovak University of Technology in Bratislava Faculty of Chemical and Food Technology, Bratislava, Slovakia (Ringgold ID: RIN201272)
,
Lukáš Kerti
2   Department of Physical Chemistry of Drugs, Comenius University in Bratislava Faculty of Pharmacy, Bratislava, Slovakia (Ringgold ID: RIN91876)
,
Miroslava Litecká
3   Institute of Inorganic Chemistry, Czech Academy of Sciences, Husinec-Řež, Czech Republic (Ringgold ID: RIN48311)
,
Ján Moncoľ
4   Institute of Inorganic Chemistry, Technology and Materials, Slovak University of Technology, Bratislava, Slovakia
,
Ivana Žideková
5   Central Laboratories, Slovak University of Technology in Bratislava, Bratislava, Slovakia (Ringgold ID: RIN61791)
,
Róbert Fischer
6   Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Bratislava, Slovakia
› Author AffiliationsSupported by: Ministerstvo školstva, vedy, výskumu a športu Slovenskej republiky VEGA, Project no. 1/0152/23
Supported by: Agentúra na Podporu Výskumu a Vývoja Project no. APVV-2023-0006
Supported by: RESEARCH AND INNOVATION AUTHORITY, “Large Project for Excellent Researchers” VAIA, Project no. 09I03-03-V03-00029
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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 the 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.



Publication History

Received: 30 September 2024

Accepted after revision: 16 December 2024

Accepted Manuscript online:
16 December 2024

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