ChemInform Abstract: Heterocycles from Carbohydrate Precursors. Part 40. Kinetic and Thermodynamic Products of Ketalization of 1-C-Substituted L-threo-Glycerol: A Regioselective Formation of 1,3-Dioxolanes.

ChemInform Abstract

The mode of ketalization of the L-threo-glycerol (IIa) with acetone (I) is investigated. The kinetic product from this reaction is the terminal dioxolane (IIb) which then partly rearranges to (IIc). The regioselectivity of the reaction and the structures of (IIb), (IIc) are studied in detail. For example, the aldehyde (V) is obtained starting from (IIb) as shown in the scheme. An independent synthesis of (IIb) is accomplished starting from the tetrahydrofuran (VI).