Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 18, Pages 5120-5123Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800494
Keywords
BOX ligands; desymmetrization; donor-acceptor cyclopropanes; Lewis acids; ureas
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Funding
- Swiss National Science Foundation (SNSF) [200021_165788, 200020_149494]
- EPFL
- Swiss National Science Foundation (SNF) [200021_165788, 200020_149494] Funding Source: Swiss National Science Foundation (SNF)
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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.
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