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Chelation‐driven Regioselective 1,2‐Dearomatizations of N‐Aromatic Zwitterions
Author(s) -
Ko Donguk,
Kim Jiyoung,
Lee Jiyoun,
Yoo Eun Jeong
Publication year - 2021
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12244
Subject(s) - chelation , chemistry , selectivity , regioselectivity , nucleophile , combinatorial chemistry , organic chemistry , catalysis
In this study, several dearomative reactions of N‐aromatic zwitterions were carried out to determine the factors controlling site selectivity. A series of organometallic species were applied as nucleophiles for dearomative additions, which revealed that chelation between metal and nitrogen anion dominantly affected the site selectivity of the dearomative reaction in N‐aromatic zwitterions. A cascade process, involving dearomative addition followed by intermolecular cyclization, to synthesize fused cyclic molecules was also demonstrated using ylides, which were selected as capable chelation substrates.