Stereoelectronic effects in the fragmentation of γ-silyloxy-β-hydroxy-α-diazocarbonyl compounds.

A series of γ-silyloxy-β-hydroxy-α-diazocarbonyl compounds were prepared as fragmentation substrates to probe the hypothesis that steric interactions between the diazo ester and adjacent silyloxy group can play an important role in determining the success of fragmentations. Proper stereoelectronic alignment of the diazo ester and the departing hydroxyl group is necessary for productive fragmentation to occur.