Highly Diastereoselective Reactions of Isoxazolidine-4,5-diols with Grignard Reagents: A New Approach to anti,syn-γ-Amino-α,β-diols

Lukáš Ďurina; Tomáš Malatinský; Ján Moncol; Ondrej Záborský; Róbert Fischer

doi:10.1055/s-0040-1706543

Synthesis, Table of Contents

Synthesis 2021; 53(04): 688-698
DOI: 10.1055/s-0040-1706543

paper

Highly Diastereoselective Reactions of Isoxazolidine-4,5-diols with Grignard Reagents: A New Approach to anti,syn-γ-Amino-α,β-diols

Lukáš Ďurina

^aInstitute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic Email: robert.fischer@stuba.sk Email: ondrej.zaborsky@stuba.sk

,

Tomáš Malatinský

^aInstitute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic Email: robert.fischer@stuba.sk Email: ondrej.zaborsky@stuba.sk

,

Ján Moncol

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

,

Ondrej Záborský∗

^aInstitute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic Email: robert.fischer@stuba.sk Email: ondrej.zaborsky@stuba.sk

,

Róbert Fischer∗

^aInstitute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovak Republic Email: robert.fischer@stuba.sk Email: ondrej.zaborsky@stuba.sk

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Abstract

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Abstract

An investigation of the reaction of 3,4-trans-isoxazolidine-4,5-diols with Grignard reagents is described for the first time. Their resemblance to five-membered cyclic hemiacetals allows them to react as α-hydroxy-β-(hydroxyamino)aldehydes in a highly stereoselective manner, providing anti,syn-γ-(hydroxyamino)-α,β-diols in moderate yields and with good to excellent syn-diastereoselectivities, which can be improved by the addition of anhydrous cerium chloride. The obtained (hydroxyamino)diols serve as suitable precursors of anti,syn-γ-amino-α,β-diols that represent valuable scaffolds for the synthesis of various biologically active compounds.

Key words - isoxazolidines - amino diols - Grignard reaction - diastereoselectivity - crystal structure

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