Suzuki Mami, Kasahara Honoka, Moriyama Katsuhiko
Department of Chemistry, Graduate School of Science and Soft Molecular Activation Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Org Lett. 2024 Oct 18;26(41):8768-8773. doi: 10.1021/acs.orglett.4c03086. Epub 2024 Oct 10.
An oxidative remote aryl rearrangement of -cinnamyl--alkoxybenzyl sulfonamides with a hypervalent iodine(III) compound was developed to furnish 5,6-disubstituted 1,3-oxazinanes in high yields. This reaction proceeded through the dearomatization of the alkoxybenzene ring on the benzyl group, which acts as a good aryl donor, inducing the regioselective installation of the aryl group and the oxygen atom via cascade transformation. An enantioselective oxidative remote aryl rearrangement using C2-symmetrical chiral iodoarene gave enantioenriched products with high enantioselectivity.
开发了一种使用高价碘（III）化合物对肉桂基-烷氧基苄基磺酰胺进行氧化远程芳基重排反应，以高产率提供5,6-二取代的1,3-恶嗪烷。该反应通过苄基上烷氧基苯环的去芳构化进行，苄基作为良好的芳基供体，通过级联转化诱导芳基和氧原子的区域选择性安装。使用C2对称手性碘芳烃进行对映选择性氧化远程芳基重排反应，得到了具有高对映选择性的对映体富集产物。
