Stereospecific 1,3‐Aminobromination of Donor–Acceptor Cyclopropanes

Sn(OTf)2‐catalyzed 1,3‐aminobromination of donor–acceptor cyclopropanes with various sulfonyl amides or electron‐poor anilines and N‐bromosuccinimide is reported. These experimentally straightforward reactions occurred with complete regio‐ and stereospecificity (for anilines) to give γ‐aminated α‐br...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-09, Vol.56 (38), p.11554-11558
Main Authors: Das, Saikat, Daniliuc, Constantin G., Studer, Armido
Format: Article
Language:English
Subjects:
1,3-aminobromination
Amides
azetidines
Bromination
Diesters
donor–acceptor cyclopropanes
N-Bromosuccinimide
Organic compounds
Stereospecificity
Substrates
γ-lactams
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Summary:Sn(OTf)2‐catalyzed 1,3‐aminobromination of donor–acceptor cyclopropanes with various sulfonyl amides or electron‐poor anilines and N‐bromosuccinimide is reported. These experimentally straightforward reactions occurred with complete regio‐ and stereospecificity (for anilines) to give γ‐aminated α‐brominated malonic diesters in good to excellent yields (up to 98 %). These compounds served as valuable substrates for subsequent reactions to provide substituted azetidines and γ‐lactams in high yields. An opening, an opportunity: Donor–acceptor cyclopropanes underwent efficient ring opening and 1,3‐aminobromination in a three‐component reaction with anilines/sulfonamides and N‐bromosuccinimide under the catalysis of Sn(OTf)2. Reactions with anilines proceeded with complete stereospecificity, and the products could be transformed into valuable azetidines and γ‐lactams.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201704092