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Organocatalytic Enantioselective Friedel–Crafts Alkylation/Lactonization Reaction of Hydroxyindoles with Methyleneoxindoles
Author(s) -
Xiao Mengjie,
Xu Dengfeng,
Liang Weihong,
Wu Wenyu,
Chan Albert S. C.,
Zhao Junling
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701089
Subject(s) - chemistry , enantioselective synthesis , friedel–crafts reaction , alkylation , benzene , indole test , ring (chemistry) , derivatization , catalysis , organic chemistry , reaction conditions , combinatorial chemistry , medicinal chemistry , high performance liquid chromatography
Functionalization of the indole benzene ring was achieved by using an organocatalytic enantioselective Friedel–Crafts alkylation/lactonization reaction of hydroxyindoles with a variety of substituted methyleneoxindoles. This reaction was applicable to indoles substituted with the hydroxy group at different positions of the benzene ring, and the corresponding pyrrolodihydrocoumarins were obtained in moderate to high yields (37–99%) with high stereoselectivities (up to 99% ee and >20:1 dr ) in most cases. A scale‐up reaction and derivatization of the representative products were also carried out to investigate the usefulness of this protocol.