Beilstein J. Org. Chem.2020,16, 1313–1319, doi:10.3762/bjoc.16.112
isoxazolidin-4-ols. The strategy relies on a highly regio- and trans-stereoselective hydroboration–oxidation reaction of the 4,5-unsubstituted 2,3-dihydroisoxazoles with basic hydrogen peroxide. The consecutive oxidation/reduction route, sequentially employing Dess–Martin periodinane and ʟ-selectride, is used
-hydroxypyrrolidines certainly makes the 4-hydroxyisoxazolidines important and valuable structural fragments in drug discovery.
Keywords: 2,3-dihydroisoxazoles; diastereoselectivity; heterocycles; hydroboration–oxidation; isoxazolidin-4-ols; Introduction
2,3-Dihydroisoxazoles (often referred to as 4-isoxazolines
hydroxylamines using malonoyl peroxide, providing N-tosylated 3-aryl-substituted 4-hydroxyisoxazolidines in a highly stereoselective manner in favor of the C-3/4-trans isomers [27]. We believe that the 3-substituted isoxazolidin-4-ols, represented by the general structures of the trans and the cis stereoisomer 3