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Synthesis of Tricyclic Isoindolones via Nickel‐Catalyzed Decyclization–Addition–Cyclization of α‐Hydroxy Ynamides
Author(s) -
Okamoto Noriko,
Yanada Reiko,
Sueda Takuya
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801207
Subject(s) - chemistry , tricyclic , isomerization , catalysis , regioselectivity , intramolecular force , ketenimine , tandem , nickel , medicinal chemistry , salt (chemistry) , condensation , combinatorial chemistry , stereochemistry , organic chemistry , materials science , physics , composite material , thermodynamics
Regioselective addition of 1,3‐dicarbonyl compounds to N ‐alkynyl‐3‐hydroxyisoindolin‐1‐ones (α‐hydroxy ynamides) was accomplished with the use of Ni II salt catalysts. The reaction proceeded by a tandem decyclization–addition–cyclization mechanism, in which a ketenimine intermediate is formed via Ni II ‐catalyzed isomerization of α‐hydroxy ynamides. The BF 3 ‐catalyzed intramolecular dehydrative condensation of the resulting α‐hydroxy enamides afforded tricyclic isoindolones in good yields.