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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 18期

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

页码：5120 / 5123

页数：4

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