Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1251-1260.DOI: 10.6023/cjoc201711045 Previous Articles     Next Articles

Articles

3-吲哚醇和色醇的催化不对称脱水芳基化反应——双吲哚取代的三芳基甲烷类化合物的不对称合成

伍平, 吴迦勒, 王静怡, 梅光建   

  1. 江苏师范大学化学与材料科学学院 徐州 221116
  • 收稿日期:2017-11-27 修回日期:2017-12-25 出版日期:2018-05-25 发布日期:2018-01-03
  • 通讯作者: 梅光建,E-mail:guangjianM@jsnu.edu.cn E-mail:guangjianM@jsnu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21702077)、江苏省自然科学基金(No.BK20170227)和徐州市应用基础研究计划(No.KH17021)资助项目.

Catalytic Asymmetric Dehydrative Arylation of 3-Indolylmethanols with Tryptophols: Enantioselective Synthesis of Bisindolyl-Substituted Triarylmethanes

Wu Ping, Wu Jiale, Wang Jingyi, Mei Guangjian   

  1. School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116
  • Received:2017-11-27 Revised:2017-12-25 Online:2018-05-25 Published:2018-01-03
  • Contact: 10.6023/cjoc201711045 E-mail:guangjianM@jsnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21702077), the Natural Science Foundation of Jiangsu Province (No. BK20170227), the Applied Fundamental Research Project of Xuzhou City (No. KH17021).

The chiral triarylmethane frameworks are featured in many biologically important molecules. As a result, the synthesis of chiral triarylmethanes has received tremendous attention from the chemists. Herein, we reported the chiral phosphoric acid catalyzed dehydrative arylation of 3-indolylmethanols with tryptophols, leading to the efficient synthesis of a series of structurally diversified chiral bisindolyl-substituted triarylmethanes in moderate to good yields (up to 80% yield) with acceptable enantioselectivities (up to 88% ee). The chiral phosphoric acid played an important role not only in the dehydration of 3-indolylmethanols, but also in the control of enantioselectivity via hydrogen-bonding and ion-pairing interactions. The only byproduct was water, indicating that this catalytic asymmetric dehydrative arylation reaction was environment-friendly and in accordance with the requirements of green chemistry. In addition, the mild reaction condition and wide substrate scope of the reaction have successfully demonstrated the great potential of organocatalysis in the chiral triarylmethanes.

Key words: triarylmethanes, organocatalysis, 3-indolylmethanols, tryptophols, green chemistry