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

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

Publication History

Received: 16 August 2020

Accepted after revision: 23 September 2020

Article published online:
29 October 2020

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