Article ID Journal Published Year Pages File Type
5278827 Tetrahedron Letters 2006 4 Pages PDF
Abstract
A convenient method for the synthesis of N-substituted C-phosphorylated nitrones 2 from hydroxymethylphosphonates via successive Swern oxidation and treatment with respective hydroxylamines is reported for the first time. Moderate (20%) to excellent (up to 90%) diastereoselectivities in cycloadditions of nitrone 2a and terminal alkenes were observed with trans C5-substituted isoxazolidines predominating. In ZnCl2-catalysed cycloadditions, mixtures enriched in cis diastereoisomers were produced.
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Physical Sciences and Engineering Chemistry Organic Chemistry
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