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
相关论文
共 26 条
  • [21] Enantioselective Lewis acid-catalyzed Mukaiyama-Michael reactions of acyclic enones.: Catalysis by allo-threonine-derived oxazaborolidinones
    Wang, XW
    Adachi, S
    Iwai, H
    Takatsuki, H
    Fujita, K
    Kubo, M
    Oku, A
    Harada, T
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26): : 10046 - 10057
  • [22] Highly Enantioselective Synthesis of Acyclic N,N′-Acetals by Chiral Urea Derived from Quinine Catalyzed the Addition of Aryl Amines to Isatin-Derived Ketimines
    Liu, Yuxin
    Wang, Jingdong
    Wei, Zhonglin
    Cao, Jungang
    Liang, Dapeng
    Lin, Yingjie
    Duan, Haifeng
    ORGANIC LETTERS, 2019, 21 (14) : 5719 - 5724
  • [23] Enantioselective aminocatalysis: Michael addition of unactivated ketones to nitroolefins catalyzed by D-fructose derived monofunctional primary amine
    Khiangte Vanlaldinpuia
    Porag Bora
    Grace Basumatary
    Rahul Mohanta
    Ghanashyam Bez
    Journal of Chemical Sciences, 2017, 129 : 1603 - 1610
  • [24] Enantioselective aminocatalysis: Michael addition of unactivated ketones to nitroolefins catalyzed by D-fructose derived monofunctional primary amine
    Vanlaldinpuia, Khiangte
    Bora, Porag
    Basumatary, Grace
    Mohanta, Rahul
    Bez, Ghanashyam
    JOURNAL OF CHEMICAL SCIENCES, 2017, 129 (10) : 1603 - 1610
  • [25] Bifunctional Primary Amine-Squaramide Catalyzed Enantioselective Intramolecular Michael Addition of Keto-enones: A Convenient Process to the Stereocontrolled Construction of trans-Dihydrobenzofuran Skeletons
    Liu, Yunting
    Lu, Aidang
    Hu, Keling
    Wang, Youming
    Song, Haibin
    Zhou, Zhenghong
    Tang, Chuchi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (22) : 4836 - 4843
  • [26] Cinchona-Based Primary Amine-Catalyzed Asymmetric Cascade Aza-Michael-Aldol Reactions of Enones with 2-(1H-Pyrrol-2-y1)-2-oxoacetates: Synthesis of Chiral Pyrrolizines with Multistereocenters
    Lee, Hyo-Jun
    Cho, Chang-Woo
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07): : 3306 - 3312