Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.