Hypervalent Iodine Oxidation of Enol Silyl Ethers using Boron Trifluoride Etherate. A Direct Route to Aryl Hydroxymethyl Ketones
Enol silyl ethers of acetophenones and acetylpyridines are oxidized to hydroxymethyl aryl ketones (ω-hydroxyacetophenones) and hydroxyacetylpyridines, respectively, using the system iodosobenzene/boron trifluoride etherate/water.
Moriarty, Robert M.,Prakash, Om,Duncan, Michael P.
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.
Moriarty, Robert M.,Duncan, Michael P.,Prakash, Om
p. 1781 - 1784
(2007/10/02)
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