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An efficient method for 3, 4‐dihydroisoquinolinium ion formation, leading to a facile introduction of nucleophiles
Author(s) -
Shimizu Makoto,
Kawamura Takato,
Fukumoto Shinya,
Mizota Isao,
Zhu Yusong
Publication year - 2021
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4211
Subject(s) - ketene , chemistry , nucleophile , acetal , reagent , silylation , carboxylate , ion , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis
The ketene silyl acetal derived from ethyl 2‐benzyltetrahydroisoquinoline‐1‐carboxylate undergoes a rapid oxidation reaction with N ‐bromosuccinimide to form 3,4‐dihydroisoquinolinium ion, which reacts with Grignard reagents to give 1,1‐disubstituted tetrahydroisoquinolines in good yields.