Gold-Catalyzed Oxidative Rearrangement Involving 1,2-Acyl Migration: Efficient Synthesis of Functionalized Dihydro-γ-Carbolines from α-(2-Indolyl) Propargylic Alcohols and Imines

被引：81
作者：
Wang, Lu [1 ]
Xie, Xin [1 ]
Liu, Yuanhong [1 ]
机构：
[1] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 50期
基金：
中国国家自然科学基金;
关键词：
1; 2-acyl migration; dihydro--carbolines; gold; homogeneous catalysis; propargylic alcohols; ONE-POT SYNTHESIS; CYCLOISOMERIZATION REACTIONS; REGIOSELECTIVE OXIDATION; INTERMOLECULAR REACTIONS; ORGANIC-REACTIONS; LEWIS ACID; DERIVATIVES; ALKYNES; CASCADE; KETONES;
D O I：
10.1002/anie.201304700
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Smooth moves with a nifty side step: A gold-catalyzed transformation of α-(2-indolyl) propargylic alcohols with imines in the presence of the oxidant 8-isopropylquinoline N-oxide provided rapid access to highly functionalized dihydro-γ-carbolines (see scheme). The reaction mechanism is proposed to involve intermolecular trapping of an α-carbonyl gold carbenoid intermediate, followed by cyclization and a novel gold-assisted 1,2-acyl migration. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：13302 / 13306
页数：5
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