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Dimethylzinc‐Mediated Chlorolactamization of Homoallylic Amines with Chloroform
Author(s) -
Nishida Yuika,
Ueda Masafumi,
Hayashi Masataka,
Takeda Norihiko,
Miyata Okiko
Publication year - 2016
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.201501241
Subject(s) - chemistry , dimethylzinc , chloroform , chloride , organic chemistry , medicinal chemistry , catalysis
A novel chlorolactamization reaction of homoallylic amines has been developed. The treatment of homoallylic amines with dimethylzinc in chloroform led to the formation of the corresponding β‐chlorolactams via the Prins‐type cyclization of a carbamoyl chloride intermediate. The results of this study highlight the synthetic utility of chloroform as a source of both carbonyl group and chloride anion.