Organocatalytic Synthesis of Chiral Tetraarylmethanes from 7-Indolylmethanols with Thioether as Directing Group
Zhengyu Han , Huiting Xu , Xinzhe Hu , Shuxuan Liu , Yang Bai , Jianhao Wang , Cuihuan Geng , Jianwei Sun , Hai Huang
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (24) : 3373 -3378.
The construction of chiral tetraarylmethanes has emerged as a rapidly developing field in organic synthesis. In previously developed strategies, the chiral tetraarylmethanes molecules were primarily based on quinone methides or 2-methyleneindoles type scaffolds, wherein the interaction between alkoxy-type "tag group" and chiral phosphoric acid played a crucial role in distinguishing between two sterically similar aryl substituents during the enantioselective nucleophilic addition step. In this work, we achieved the first synthesis of chiral tetraarylmethanes based on 7-indole imine methides, in which the methylthio "type tag" group is pivotal for achieving effective chiral recognition, rather than the conventional alkoxy group. Furthermore, subsequent derivatization of the chiral products and their evaluation in anti-cancer assays underscore the synthetic and biological significance of these structurally unique 7-indole containing tetraarylmethane derivatives.
7-Indole imine methides / Enantioselective addition / Organocatalysis / Chiral tetraarylmethanes / Anti-cancer activity
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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