Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel-Crafts alkylation/ketalization sequence
Jiao-Mei Guo1, Wen-Bo Wang1, Jia Guo1
1Institute of Functional Organic Molecular Engineering, College of Chemistry and Chemical Engineering, Henan University Kaifeng 475004 China wangqilin@henu.edu.cn buzhanwei@henu.edu.cn.
Abstract:
The first TfOH-catalyzed three-component Friedel-Crafts alkylation/ketalization sequence of indoles, alcohols and ortho-hydroxychalcones was developed to afford a wide range of 4-indole substituted chromans bearing a ketal motif in 77-99% yields. Notably, only a simple filtration was needed to purify them. By altering methanol to CHCl3, 2,4-bisindole substituted chroman with the same indole substituent at the C2 and C4 positions was afforded. Moreover, 2,4-bisindole substituted chromans with different indole substituents could be obtained by treatment of 4-indole monosubstituted chromans with another indole molecule.
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