Ring-Closing Metathesis/Isomerization/Pictet-Spengler Cascade via Ruthenium/Chiral Phosphoric Acid Sequential Catalysis

被引:107
作者
Cai, Quan [1 ]
Liang, Xiao-Wei [1 ]
Wang, Shou-Guo [1 ]
Zhang, Jun-Wei [1 ]
Zhang, Xiao [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
ENANTIOSELECTIVE BRONSTED ACID; BIOMIMETIC ASYMMETRIC HYDROGENATION; NONREARRANGED MONOTERPENOID UNIT; ACYLIMINIUM CYCLIZATION CASCADES; SIMPLE INDOLE ALKALOIDS; PICTET-SPENGLER; RELAY CATALYSIS; BINARY-SYSTEM; COOPERATIVE CATALYSIS; 3-COMPONENT REACTIONS;
D O I
10.1021/ol302215u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral phosphoric acid worked together with Hoveyda-Grubbs II catalyst enabling highly efficient synthesis of enantioenriched tetrahydro-beta-carbolines (up to 98% yield, 99% ee) through a ring-closing metathesis/isomerization/Pictet-Spengler cascade reaction via sequential catalysis.
引用
收藏
页码:5022 / 5025
页数:4
相关论文
共 67 条
  • [1] Synthesis of Heterocycles through a Ruthenium-Catalyzed Tandem Ring-Closing Metathesis/Isomerization/N-Acyliminium Cyclization Sequence
    Ascic, Erhad
    Jensen, Jakob F.
    Nielsen, Thomas E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) : 5188 - 5191
  • [2] Enantioselective Intramolecular Aza-Michael Additions of Indoles Catalyzed by Chiral Phosphoric Acids
    Cai, Quan
    Zheng, Chao
    You, Shu-Li
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) : 8666 - 8669
  • [3] Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis
    Cai, Quan
    Zhao, Zhuo-An
    You, Shu-Li
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (40) : 7428 - 7431
  • [4] Ru-catalyzed tandem cross-metathesis/intramolecular-hydroarylation sequence
    Chen, Jia-Rong
    Li, Chang-Feng
    An, Xiao-Lei
    Zhang, Ji-Ji
    Zhu, Xiao-Yu
    Xiao, Wen-Jing
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) : 2489 - 2492
  • [5] Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation
    Chen, Qing-An
    Gao, Kai
    Duan, Ying
    Ye, Zhi-Shi
    Shi, Lei
    Yang, Yan
    Zhou, Yong-Gui
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (04) : 2442 - 2448
  • [6] Biomimetic Asymmetric Hydrogenation: In Situ Regenerable Hantzsch Esters for Asymmetric Hydrogenation of Benzoxazinones
    Chen, Qing-An
    Chen, Mu-Wang
    Yu, Chang-Bin
    Shi, Lei
    Wang, Duo-Sheng
    Yang, Yan
    Zhou, Yong-Gui
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) : 16432 - 16435
  • [7] Convergent Asymmetric Disproportionation Reactions: Metal/Bronsted Acid Relay Catalysis for Enantioselective Reduction of Quinoxalines
    Chen, Qing-An
    Wang, Duo-Sheng
    Zhou, Yong-Gui
    Duan, Ying
    Fan, Hong-Jun
    Yang, Yan
    Zhang, Zhang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) : 6126 - 6129
  • [8] Catalytic Asymmetric Pictet-Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines
    Cheng, Dao-Juan
    Wu, Hai-Bian
    Tian, Shi-Kai
    [J]. ORGANIC LETTERS, 2011, 13 (20) : 5636 - 5639
  • [9] Asymmetric synthesis of isoquinoline alkaloids
    Chrzanowska, M
    Rozwadowska, MD
    [J]. CHEMICAL REVIEWS, 2004, 104 (07) : 3341 - 3370
  • [10] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION
    COX, ED
    COOK, JM
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1797 - 1842