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Lewis Acid‐Catalyzed Annulation of Propargylic Alcohols with ( Z )‐2‐Styryl‐1 H ‐Indoles
Author(s) -
Li XueSong,
Han YaPing,
Zhu XinYu,
Xia Yu,
Wei WanXu,
Li Ming,
Liang YongMin
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.201800907
Subject(s) - chemistry , annulation , trifluoromethanesulfonate , catalysis , isomerization , carbazole , cascade , lewis acids and bases , combinatorial chemistry , intermolecular force , stereochemistry , organic chemistry , medicinal chemistry , molecule , chromatography
A novel copper(II) trifluoromethanesulfonate‐catalyzed intermolecular cascade annulation strategy for the construction of a great variety of pentacyclic compounds possessing valuable carbazole fragments was developed employing propargylic alcohols and ( Z )‐2‐styryl‐1 H ‐indoles as the initial substrates. This protocol, which entails a sequential Meyer‐Schuster rearrangement/isomerization/‐cyclization cascade, enables facile and atom‐economical access to various pentacyclic compounds with broad functional‐group tolerance in good yields under mild conditions. The conversion could be efficiently scaled up to gram quantities, accentuating a potential application of this work.