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
收藏
页码：13854 / 13857
页数：4
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