Palladium(0)-Catalyzed Enantioselective C-H Arylation of Cyclopropanes: Efficient Access to Functionalized Tetrahydroquinolines

被引：156
作者：
Saget, Tanguy [1 ,2 ]
Cramer, Nicolai [1 ]
机构：
[1] EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland
[2] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 51期
基金：
欧洲研究理事会;
关键词：
asymmetric catalysis; C?H activation; cyclopropanes; palladium; tetrahydroquinolines; INTRAMOLECULAR ALKANE ARYLATION; C(SP(3))-H ACTIVATION; FUSED INDOLINES; BONDS; DERIVATIVES; ACIDS; METALATION; ARCHITECTURES; DEPROTONATION; MECHANISM;
D O I：
10.1002/anie.201207959
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Activated: The title reaction proceeds efficiently with 1 mol % of palladium and gives tetrahydroquinolines in excellent enantioselectivities (see scheme). The enantiodiscriminating concerted metalation-deprotonation step occurs via a rare seven-membered palladacycle. The cyclopropyl-substituted tetrahydroquinolines can be regioselectively and enantiospecifically reduced to chiral tetrahydrobenzoazepines. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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收藏
页码：12842 / 12845
页数：4
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