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Paper | Special issue | Vol 95, No. 2, 2017, pp.787-798
Published online, 1st November, 2016
DOI: 10.3987/COM-16-S(S)42
Triphosgene-Mediated Chlorolactamization and Aminolactamization of Homoallylic Amines

Yuika Nishida, Norihiko Takeda, Okiko Miyata,* and Masafumi Ueda*

*Department of Medicinal Chemistry, Kobe Pharmaceutical University, 4-19-1, Motoyamakitamachi, Higashinada, Kobe 658-8558, Japan


Two types of aminocarbonylation reaction of homoallylic amines have been developed. The treatment of homoallylic amines with triphosgene in dichloromethane led to formation of the corresponding β-chlorolactams via Prins-type cyclization of a carbamoyl chloride intermediate. For the reaction in acetonitrile, β-aminolactams were obtained via sequential Prins-type cyclization and Ritter-type reactions.