5-Methyl-4H-1,3-dioxins, new chiral building blocks: transformation into (R)- and (S)-4-hydroxymethyl-4-METHYL-1,3-DIOXOLANE (cas 1072-47-5)s via oxidation and rearrangement and determination of the absolute configuration

Add time:07/26/2019    Source:sciencedirect.com

5-Methyl-4H-1,3-dioxins obtained by asymmetric double-bond isomerization have been transformed into 4-hydroxymethyl-4-methyl-1,3-dioxolanes by m-chloroperbenzoic acid oxidation, ring contraction and reduction. The stereochemical course of this transformation has been studied, while the relative configuration of the intermediate oxidation product and the absolute configuration of the resulting camphanyl ester of 2-tert-butyl-4-hydroxymethyl-4-methyl-1,3-dioxolane was established by X-ray crystallography. From these results, the absolute configuration of the dioxins has been deduced.

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