Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor-Acceptor meso-Diaminocyclopropanes

Daniele Perrotta; Ming-Ming Wang; Jérôme Waser

doi:10.1002/anie.201800494

Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor-Acceptor meso-Diaminocyclopropanes

Angew Chem Int Ed Engl. 2018 Apr 23;57(18):5120-5123. doi: 10.1002/anie.201800494. Epub 2018 Mar 23.

Authors

Daniele Perrotta¹, Ming-Ming Wang¹, Jérôme Waser¹

Affiliation

¹ Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland.

PMID: 29461662
DOI: 10.1002/anie.201800494

Abstract

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.

Keywords: BOX ligands; Lewis acids; desymmetrization; donor-acceptor cyclopropanes; ureas.

Publication types

Research Support, Non-U.S. Gov't