The need for an incisive analysis of the regioselectivity associated with the deprotonation of alpha-alkoxy and alpha-acyloxy ketones

A summary of informative examples involving the regioselective deprotonatio n of a-oxygenated ketones has been compiled from the literature and augment ed by new findings from the authors' laboratory. The text provides a brief discussion of the complexity of the matter. The data are tabulated with reg ard to enolization both away from and toward the oxygen substituent, with s ubsequent capture at oxygen or carbon. The possible role of steric, electro nic, and conformational factors is addressed in a manner that points up the need for a more detailed understanding of these enolizations as a general process.