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Issue 28, 2018, Issue in Progress
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Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel–Crafts alkylation/ketalization sequence

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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.

Graphical abstract: Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel–Crafts alkylation/ketalization sequence

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Article information


Submitted
21 Mar 2018
Accepted
13 Apr 2018
First published
25 Apr 2018

This article is Open Access

RSC Adv., 2018,8, 15641-15651
Article type
Paper

Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel–Crafts alkylation/ketalization sequence

J. Guo, W. Wang, J. Guo, Y. Zhu, X. Bai, S. Jin, Q. Wang and Z. Bu, RSC Adv., 2018, 8, 15641
DOI: 10.1039/C8RA02481B

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