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Paper | Regular issue | Vol 41, No. 10, 1995, pp.2233-2244
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7146
Synthesis and Stereochemistry of Chiral 1,3-Dioxanic Compounds Obtained from α-Alkylated β-Ketoesters

Ion Grosu* , Sorin Mager, Gérard Plé, Roberto Martinez, Luminita Muntean, and Eugen Mesaros

*Instituto de Química, Universidad Nacional Autónama de México, Ciudad Universitaria, Circuito Exterior, Mexico D.F., 04510, Mexico

Abstract

1,3-Dioxanic compounds were obtained by the ketalisation reaction of some α-alkylated β-ketoesters. The conformational analysis by means of 1H- and 13C-nmr investigations showed the anancomeric structure of the compounds. The axial or the equatorial position of the groups was inferred by N.O.E. experiments. The influence of the chiral carbon atom of the esteric group located at C2 was studied using the diastereotopicity of the protons and of the carbon atoms recorded in high field nmr spectra.