Versatile Access to Chiral Indolines by Catalytic Asymmetric Fischer Indolization

被引：62
|
作者：
Martinez, Alberto [1 ]
Webber, Matthew J. [1 ]
Mueller, Steffen [1 ]
List, Benjamin [1 ]
机构：
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 36期
关键词：
BrOnsted acid catalysis; Fischer indole synthesis; heterocycles; indoline; organocatalysis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; INTRAMOLECULAR CARBOLITHIATION; PHOSPHORIC-ACIDS; 3-SUBSTITUTED INDOLINES; HYDROGENATION; INDOLES; CASCADE; PYRROLOINDOLINES; CONSTRUCTION; CYCLIZATION;
D O I：
10.1002/anie.201301618
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
"Fisching" for complexity: The chiral Brønsted acid (R)-STRIP catalyzes the asymmetric Fischer indolization of a range of monosubstituted cyclopentanones and cyclohexanones to give chiral fused indolines bearing a quaternary stereogenic center at the 3-position. The method has been extended to include substrates bearing a tethered nucleophile, thus allowing for enantioselective indolization/ring-closing cascades to complex propellanes featuring two vicinal quaternary stereocenters. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9486 / 9490
页数：5
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