Hypervalent Iodine Oxidation of Silyl Enol Ethers. A Direct Route to α-Hydroxy Ketones.

Hypervalent iodine oxidation of various silyl enol ethers (aromatic, heteroaromatic, and aliphatic) using iodosobenzene–boron trifluoride diethyl ether–water provides a general and direct route for the α-hydroxylation of ketones. The structures of 2-hydroxy-(8) and 3-hydroxy-acetylpyridine (9) are discussed as well as the scope and mechanism of the reaction.