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

被引:55
作者
Perrotta, Daniele [1 ]
Wang, Ming-Ming [1 ]
Waser, Jerome [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, EPFL SB ISIC LCSO, BCH 4306, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
BOX ligands; desymmetrization; donor-acceptor cyclopropanes; Lewis acids; ureas; CYCLOPROPYL KETONES; MARINE SPONGE; CYCLOADDITION REACTIONS; BIS(OXAZOLINE) LIGANDS; ASYMMETRIC CATALYSIS; 3+2 ANNULATION; ALKALOIDS; DERIVATIVES; WATER; SEA;
D O I
10.1002/anie.201800494
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:5120 / 5123
页数:4
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