Catalytic Enantioselective 1,3-Alkyl Shift in Alkyl Aryl Ethers: Efficient Synthesis of Optically Active 3,3′-Diaryloxindoles

Catalytic Enantioselective 1,3-Alkyl Shift in Alkyl Aryl Ethers: Efficient Synthesis of Optically Active 3,3′-Diaryloxindoles
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DOI:
10.1002/anie.201801650
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发表时间:
2018-05-14
影响因子:
16.6
通讯作者:
Patil, Nitin T.
Patil, Nitin T.
中科院分区:
化学1区
文献类型:
--
作者:
Gade, Amol B.;Bagle, Pradip N.;Patil, Nitin T.

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首次报道了在手性Bronsted酸催化下烷基芳基醚的有机催化不对称1,3-烷基转移反应合成手性3,3‘-二芳氧基吲哚。初步实验结果表明,3,3‘-二芳氧基吲哚的每个对映体和外消旋混合物对HeLa细胞具有不同的抑制增殖活性。
Reported is the first organocatalytic asymmetric 1,3-alkyl shift in alkyl aryl ethers for the synthesis of chiral 3,3'-diaryloxindoles using a chiral Bronsted acid catalyst. Preliminary results showed that each enantiomer of the 3,3'-diaryloxindole, and a racemic mixture, showed different antiproliferative activities against HeLa cell lines by using an MTT assay.