Collect. Czech. Chem. Commun. 1980, 45, 888-891

Stereoselective photochemical addition of acetaldehyde to the products of Clauson-Kaas reaction

Jan Šrogl, Miroslav Janda, František Liška and Ivan Stibor

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Photochemical addition of acetaldehyde to 2,5-dimethoxy-2,5-dihydrofuran (I) (and the pure stereoisomers Ia and Ib), methyl 2,5-dimethoxy-2,5-dihydrofuran-2-carboxylate (II), methyl 2,5-dimethoxy-2,5-dihydrofuran-3-carboxylate (III) and cis-2-hydroxymethyl-2,5-dimethoxy-2,5-dihydrofuran (IV) was studied. The acetyl group enters into the position 4 of the arising tetrahydrofuran system, trans relative to the ester or hydroxymethyl group in the position 2.