Construction of CF(3)-Containing Tetrahydropyrano[3,2-b]indoles through DMAP-Catalyzed [4+1]/[3+3] Domino Sequential Annulation.
Construction of CF(3)-Containing Tetrahydropyrano[3,2-b]indoles through DMAP-Catalyzed [4+1]/[3+3] Domino Sequential Annulation.
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通过 DMAP 催化的 [4 1]/[3 3] 多米诺顺序成环构建含 CF(3) 的四氢吡喃并[3,2-b]吲哚。
DOI：
10.1021/acs.orglett.0c02164
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Huang You
中科院分区：
文献类型：
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作者：
Zhu Yannan;Huang You
报道了邻氨基三氟苯乙酮衍生物与β‘-乙酰氧基烯丙酸酯在DMAP作用下的[4+1]/[3+3]多米诺连续环化反应。在温和的反应条件下，以高产率(≤98%)合成了多种含CF3的四氢吡喃并[3，2-b]吲哚。该反应可以在一步内依次生成一个C-N键、一个C-C键和一个C-O键。通过克级反应和产物的各种转化证明了合成的实用性。
A [4+1]/[3+3] domino sequential annulation reaction ofo-aminotrifluoroacetophenone derivatives and β′-acetoxy allenoates enabled by DMAP has been reported. A variety of CF3-containing tetrahydropyrano[3,2-b]indoles were obtained as a single diastereomer in high yields (≤98%) under mild conditions. The reaction can build one C–N bond, one C–C bond, and one C–O bond sequentially in a single step. The synthetic utility was demonstrated with gram-scale reactions and various transformations of the products.