通过氮杂 Cope 重排，快速合成对映纯反式-3-芳基哌嗪-2-羧酸衍生物。
Short synthesis of enantiopure trans-3-arylpiperazine-2-carboxylic acid derivatives via diaza-Cope rearrangement.
机构信息
Department of Chemistry, College of Natural Sciences, Seoul National University , Seoul 151-747, South Korea, and Department of Chemistry, University of Toronto , Toronto, Ontario M5S 3H6, Canada.
出版信息
Org Lett. 2012 Jul 20;14(14):3664-7. doi: 10.1021/ol301506b. Epub 2012 Jul 6.
An efficient synthetic method was developed for the construction of enantiomerically pure trans-3-arylpiperazine-2-carboxylic acid derivatives using diaza-Cope rearrangement (DCR) as a key step starting from (R,R)/(S,S)-1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (HPEN). A complete transfer of stereochemical integrity was observed for the transformation. Piperazine ring formation from the chiral 1,2-ethylenediamine derivatives using diphenylvinylsulfonium triflate followed by oxidation using ruthenium(III) chloride monohydrate in the presence of sodium periodate provided the desired enantiopure trans-3-arylpiperazine-2-carboxylic acid derivatives.
开发了一种从（R,R）/（S,S）-1,2-双（2-羟基苯基）-1,2-二氨基乙烷（HPEN）出发，通过氮杂-Cope 重排（DCR）作为关键步骤，构建对映纯反式-3-芳基哌嗪-2-羧酸衍生物的有效合成方法。观察到该转化完全转移了立体化学完整性。使用二苯基乙烯基砜三氟甲磺酸盐从手性 1,2-乙二胺衍生物中形成哌嗪环，然后在高碘酸钠存在下使用氯化钌（III）一水合物氧化，得到所需的对映纯反式-3-芳基哌嗪-2-羧酸衍生物。
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