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

Lukáš Ďurina; Lukáš Kerti; Miroslava Litecká; Ján Moncol; Ivana Žídeková; Róbert Fischer

doi:10.1055/a-2503-2981

Synthesis, Inhaltsverzeichnis

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

paper

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

Authors

Lukáš Ďurina ∗

^aInstitute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic
Lukáš Kerti

^bDepartment of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32 Bratislava, Slovak Republic
Miroslava Litecká

^cInstitute of Inorganic Chemistry of the Czech Academy of Sciences, 250 68 Husinec-Řež, č.p. 1001, Czech Republic
Ján Moncol

^dInstitute of Inorganic Chemistry, Technology and Materials, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic
Ivana Žídeková

^eCentral Laboratories, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic
Róbert Fischer

^aInstitute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic

Abstract

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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 structures

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Referenzen

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