Synthesis 2025; 57(06): 1213-1222
DOI: 10.1055/a-2503-2981
paper

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

a   Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic
,
Lukáš Kerti
b   Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32 Bratislava, Slovak Republic
,
Miroslava Litecká
c   Institute of Inorganic Chemistry of the Czech Academy of Sciences, 250 68 Husinec-Řež, č.p. 1001, Czech Republic
,
Ján Moncol
d   Institute of Inorganic Chemistry, Technology and Materials, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic
,
Ivana Žídeková
e   Central Laboratories, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic
,
Róbert Fischer
a   Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic
› Author Affiliations
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.

Supporting Information



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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