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

作者：Takesue Takuya; Fujita Morifumi^*; Sugimura Takashi; Akutsu Hiroki

来源：Organic Letters, 2014, 16(17): 4634-4637.

DOI：10.1021/ol502225p

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.

• 出版日期2014-9-5