Metal-Free Enantioselective Electrophilic Activation of Allenamides: Stereoselective Dearomatization of Indoles

被引：123

作者：

Romano, Ciro ^{[1
]}

Jia, Minqiang ^{[1
]}

Monari, Magda ^{[1
]}

Manoni, Elisabetta ^{[1
]}

Bandini, Marco ^{[1
]}

机构：

[1] Alma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, I-40126 Bologna, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 50期

关键词：

BrOnsted acids; dearomatization; enantioselectivity; homogeneous catalysis; indoles; ASYMMETRIC TRANSFER HYDROGENATION; ALPHA-IMINO ESTERS; FRIEDEL-CRAFTS REACTION; PHOSPHORIC-ACID; BRONSTED ACIDS; CYCLOADDITION; ALKENES; FLUORINATION; CYCLIZATION; REDUCTION;

D O I：

10.1002/anie.201407518

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The effective and unprecedented chiral BINOL phosphoric acid catalyzed (1-10mol%) dearomatization of indoles through electrophilic activation of allenamides (ee up to 94%), is documented. Besides the synthesis of 3,3-disubstituted indolenine cores, a dearomatization/hydrogen transfer cascade sequence is also presented as a new synthetic shortcut toward highly enantiomerically enriched indolines.

引用

页码：13854 / 13857

页数：4

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