Rui Kanghua, Shen Hanxiao, Lin Xufeng
Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
J Org Chem. 2024 Oct 4;89(19):14348-14360. doi: 10.1021/acs.joc.4c01772. Epub 2024 Sep 16.
A novel asymmetric (4 + 3) cycloaddition of indole-2,3-quinodimethanes in situ generated from 3-methyl-2-indolylmethanols with 3-indolylmethanols via chiral phosphoric acid catalysis has been established. The cycloaddition reaction exhibits a broad substrate scope affording the diverse enantioenriched cyclohepta fused diindoles in high yields with good enantioselectivities. Significantly, this work represents the first application of 3-methyl-2-indolylmethanols as 4C synthons instead of the commonly reported three-atom synthons in cycloaddition reactions.
通过手性磷酸催化，由3-甲基-2-吲哚甲醇原位生成的吲哚-2,3-醌二甲烷与3-吲哚甲醇之间实现了一种新型的不对称(4 + 3)环加成反应。该环加成反应具有广泛的底物范围，能以高产率和良好的对映选择性提供多种对映体富集的环庚烷稠合二吲哚。值得注意的是，这项工作首次将3-甲基-2-吲哚甲醇用作4C合成子，而非环加成反应中常见报道的三原子合成子。
