Substitution-Controlled Selective Formation of Hexahydrobenz[e]isoindoles and 3‑Benzazepines via In(OTf)3‑Catalyzed Tandem Annulations

A dramatic N-substituent controlled tandem annulation of 2-(2-(2-bromoethyl)­phenyl)-1-sulfonylaziridines with 1,3-dicarbonyl compounds has been developed. When the N-substituent was a 4-methylbenzenesulfonyl group (Ts), sequential ring opening of aziridines, nucleophilic substitution, and lactamiza...

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Published inOrganic letters Vol. 20; no. 18; pp. 5680 - 5683
Main Authors Xing, Siyang, Gu, Nan, Wang, Xin, Liu, Jingyi, Xing, Chunyan, Wang, Kui, Zhu, Bolin
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.09.2018
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Summary:A dramatic N-substituent controlled tandem annulation of 2-(2-(2-bromoethyl)­phenyl)-1-sulfonylaziridines with 1,3-dicarbonyl compounds has been developed. When the N-substituent was a 4-methylbenzenesulfonyl group (Ts), sequential ring opening of aziridines, nucleophilic substitution, and lactamization took place to provide a series of hexahydrobenz­[e]­isoindole compounds in good yields with good diastereoselectivities. By contrast, 3-benzazepine compounds were afforded in good yields via ring opening of aziridines and nucleophilic substitution when the N-substituent was the 4-nitrobenzenesulfonyl group (Ns).
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02406