Hypervalent iodine oxidation of silyl enol ethers. A direct route to α-hydroxy ketones
Abstract
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.