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Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor–Acceptor meso ‐Diaminocyclopropanes
Author(s) -
Perrotta Daniele,
Wang MingMing,
Waser Jérôme
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201800494
Subject(s) - enantioselective synthesis , desymmetrization , chemistry , oxazoline , pyrrole , lewis acids and bases , catalysis , tsuji–trost reaction , ligand (biochemistry) , alkylation , ring (chemistry) , organic chemistry , combinatorial chemistry , stereochemistry , biochemistry , receptor
The first Lewis acid catalyzed enantioselective ring‐opening desymmetrization of a donor–acceptor meso ‐diaminocyclopropane is reported. The copper(II)‐catalyzed Friedel–Crafts alkylation of indoles and one pyrrole with an unprecedented meso ‐diaminocyclopropane delivered enantioenriched, diastereomerically pure urea products, which are structurally related to natural and synthetic bioactive compounds. The development of a new ligand through the investigation of an underexplored subclass of bis(oxazoline) ligands was essential for achieving high enantioselectivities.