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A Series of Two Oxidation Reactions of ortho-Alkenylbenzamide with Hypervalent Iodine(III): A Concise Entry into (3R,4R)‑4-Hydroxymellein and (3R,4R)‑4-Hydroxy-6-methoxymellein

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posted on 05.09.2014, 00:00 authored by Takuya Takesue, Morifumi Fujita, Takashi Sugimura, Hiroki Akutsu
A sequence of oxidation reactions of alkenamides with hypervalent iodine is described. Oxidation of ortho-alkenylbenzamide substrates selectively gave isochroman-1-imine products. The products underwent further oxidation in the presence of a Pd salt catalyst leading to regioselective C–H acetoxylation at the 8-position. A series of oxidations was applied to the crucial steps of asymmetric synthesis of 4-hydroxymellein derivatives.