Enantioselective Michael/Mannich Polycyclization Cascade of Indolyl Enones Catalyzed by Quinine-Derived Primary Amines

被引:108
作者
Cai, Quan [1 ]
Zheng, Chao [1 ]
Zhang, Jun-Wei [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
amines; asymmetric catalysis; cascade reactions; indoles; organocatalysis; DIELS-ALDER REACTION; SIMPLE ALPHA; BETA-UNSATURATED KETONES; ORGANOCATALYTIC CONJUGATE ADDITION; FRIEDEL-CRAFTS ALKYLATION; ALPHA-BRANCHED ENALS; MICHAEL ADDITION; MULTISUBSTITUTED CYCLOPENTANES; QUATERNARY STEREOCENTERS; ASYMMETRIC EPOXIDATION; IMINIUM ACTIVATION;
D O I
10.1002/anie.201103937
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three's a crowd: The title reaction provides a tetracylic core bearing three chiral centers (see scheme; Ts=4-toluenesulfonyl) with excellent enantioselectivity and good diastereoselectivity. The reaction was used to efficiently construct the (+)-kreysiginine skeleton. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8665 / 8669
页数:5
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