烯烃-和-Oxyamination 与丙二酰过氧化物。
Alkene - and -Oxyamination with Malonoyl Peroxides.
机构信息
Department of Pure and Applied Chemistry, WestCHEM, Thomas Graham Building , University of Strathclyde , 295 Cathedral Street , Glasgow G1 1XL , U.K.
GlaxoSmithKline Medicines Research Centre , Gunnels Wood Road , Stevenage SG1 2NY , U.K.
出版信息
Org Lett. 2020 Feb 21;22(4):1659-1664. doi: 10.1021/acs.orglett.0c00253. Epub 2020 Jan 30.
Malonoyl peroxide is an effective reagent for the - or -oxyamination of alkenes. Reaction of and an alkene in the presence of --butyl--tosylcarbamate (R = COBu) leads to the -oxyaminated product in up to 99% yield. Use of -methyl--tosyl carbamate (R = COMe) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the -oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.
丙二酰过氧化物是烯烃 α-或β-羟胺化的有效试剂。在 - 丁基 - 对甲苯磺酰胺（R = COBu）的存在下，与烯烃反应可得到高达 99%产率的 α-羟胺化产物。使用 - 甲基 - 对甲苯磺酰胺（R = COMe）作为氮亲核试剂，然后用三氟乙酸处理产物，可得到高达 77%产率的 β-羟胺化产物。提出了与观察到的选择性一致的反应机制。
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