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Stereospecific 1,3‐Aminobromination of Donor–Acceptor Cyclopropanes
Author(s) -
Das Saikat,
Daniliuc Constantin G.,
Studer Armido
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704092
Subject(s) - stereospecificity , chemistry , acceptor , sulfonyl , medicinal chemistry , electron acceptor , organic chemistry , catalysis , physics , alkyl , condensed matter physics
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.