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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 37期

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

页码：8665 / 8669

页数：5

共 26 条

[1] Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines
Zhai, Xian-Dong
Yang, Zhong-Duo
Luo, Zhi
Xu, Hong-Tao
CHINESE CHEMICAL LETTERS, 2017, 28 (08) : 1793 - 1797
[2] Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines
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ChineseChemicalLetters, 2017, 28 (08) : 1793 - 1797
[3] Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine
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Kim, Yoon-Jung
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[4] Quinine-Derived Thiourea and Squaramide Catalyzed Conjugate Addition of α-Nitrophosphonates to Enones: Asymmetric Synthesis of Quaternary α-Aminophosphonates
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JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 1402 - 1413
[5] Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides
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[6] Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides
Jie Wang
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[7] Enantioselective Michael Addition of Cyclic β-Diones to α,β-Unsaturated Enones Catalyzed by Quinine-Based Organocatalysts
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Wang, Wei
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MOLECULES, 2017, 22 (07):
[8] Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides
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Xin Li
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[9] Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides
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[10] Asymmetric Organocatalytic Michael Addition of Pyrroles to Enones by Cinchona Alkaloid-Derived Primary Amines
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Enders, Dieter
SYNTHESIS-STUTTGART, 2013, 45 (20): : 2904 - 2912

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