Pd-Catalyzed Asymmetric Dearomative Cycloaddition for Construction of Optically Active Pyrroloindoline and Cyclopentaindoline Derivatives: Access to 3a-Aminopyrroloindolines.
Pd-Catalyzed Asymmetric Dearomative Cycloaddition for Construction of Optically Active Pyrroloindoline and Cyclopentaindoline Derivatives: Access to 3a-Aminopyrroloindolines.
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DOI：
10.1021/acs.joc.8b00046
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发表时间：
2018-02
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影响因子：
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通讯作者：
Junqi Zhang;Feifei Tong;Bingbing Sun;Weitai Fan;Jun-Bo Chen;Dandan Hu;Xing-Wang Wang-Xing-Wang-Wang-2426252
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文献类型：
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作者：
Junqi Zhang;Feifei Tong;Bingbing Sun;Weitai Fan;Jun-Bo Chen;Dandan Hu;Xing-Wang Wang-Xing-Wang-Wang-2426252
在手性box/Pd（0）配合物存在下，成功地研究了3-硝基吲哚分别与乙烯基氮丙啶和乙烯基环丙烷的不对称脱芳[3 + 2]环加成反应.以高产率、良好的区域选择性、化学选择性和对映体选择性，顺利获得了一系列富含对映体的含有三个连续手性中心的3a-硝基-六氢吡咯并[2，3-B]吲哚和8 b-硝基六氢环戊并[B]吲哚衍生物。值得注意的是，该方法的合成效用通过所需产物的碳-碳双键的直接还原胺化和官能化来证明。
Asymmetric dearomative [3 + 2] cycloaddition reactions of 3-nitroindoles with vinyl aziridine and vinyl cyclopropanes have been respectively successfully developed in the presence of a chiral box/Pd(0) complex. A series of enantiomerically enriched 3a-nitro-hexahydropyrrolo[2,3-b]indole and 8b-nitrohexahydrocyclopenta[b]indole derivatives containing three contiguous chiral centers are smoothly obtained in high yields with satisfactory regio-, chemo-, and enantioselectivity. Remarkably, the synthetic utility of this process was demonstrated through direct reductive amination and functionalization of the carbon-carbon double bond of the desired products.