The stereochemical fate of C-4 in a l13-dioxan-2-one in its decomposition to a 2-substituted thietane has been examined. Lithium aluminum hydride reduction of (R)-(-)-3-acetoxybutyric acid, obtained from quinine resolution of@-hydroxybutyric acid, afforded (R)-(-)-l13- butanediol. This diol was then converted to (E)-(-)-4-methyl-1, 3-dioxan-2-one, which was in turn heated with potassium thiocyanate at 170-180". The resulting thietane was oxidized ...
