Gold-Catalyzed Cycloisomerization/1,5-H Migration/Diels-Alder Reaction Cascade: Synthesis of Complex Nitrogen-Containing Heterocycles

被引：33
|
作者：
Zhang, Shuyao [1 ]
Cheng, Beiming [1 ]
Wang, Shen-An [1 ]
Zhou, Ling [1 ,3 ]
Tung, Chen-Ho [1 ]
Wang, Jianwu [1 ]
Xu, Zhenghu [1 ,2 ]
机构：
[1] Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, Educ Minist, Jinan 250100, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] Miami Univ, Dept Chem & Biochem, Oxford, OH 45056 USA
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 05期
关键词：
C-H BOND; HIGHLY ENANTIOSELECTIVE SYNTHESIS; BIMETALLIC RELAY CATALYSIS; TERMINAL ALKYNES; CHIRAL ALLENES; ACID CATALYSIS; FUNCTIONALIZATION; DERIVATIVES; ACTIVATION; PLATINUM;
D O I：
10.1021/acs.orglett.7b00090
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unprecedented gold-catalyzed cydoisomerization/1,5-H migration/Diels-Alder reaction cascade has been developed that enables the rapid construction of complex nitrogen polycyclic compounds. This one-pot, three-step cascade reaction offers good yields of the products and is promoted by a single gold catalyst under very mild conditions.
引用
收藏
页码：1072 / 1075
页数：4
相关论文
共 29 条
  • [1] SYNTHESIS OF NITROGEN-CONTAINING HETEROCYCLES BY THE IMINO DIELS-ALDER REACTION
    WEINREB, SM
    LEVIN, JI
    HETEROCYCLES, 1979, 12 (07) : 949 - 975
  • [2] A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
    Artigas, Albert
    Vila, Jordi
    Lledo, Agusti
    Sola, Miguel
    Pla-Quintana, Anna
    Roglans, Anna
    ORGANIC LETTERS, 2019, 21 (17) : 6608 - 6613
  • [3] Gold-Catalyzed Cycloisomerization and Diels-Alder Reaction of 1,6-Diyne Esters with Alkenes and Diazenes to Hydronaphthalenes and -cinnolines
    Yan, Jianming
    Tay, Guan Liang
    Neo, Cuien
    Lee, Bo Ra
    Chan, Philip Wai Hong
    ORGANIC LETTERS, 2015, 17 (17) : 4176 - 4179
  • [4] Gold-Catalyzed [1,5]-Hydride Shift onto Unactivated Alkynes To Trigger an Intermolecular Diels-Alder Reaction
    Wu, Xiang
    Chen, Shu-Sen
    Hu, Yue
    Gong, Liu-Zhu
    ORGANIC LETTERS, 2014, 16 (14) : 3820 - 3823
  • [5] Gold-catalyzed synthesis of nitrogen-containing heterocycles from ε-N-protected propargylic esters
    Huang, Jianfeng
    Huang, Xuan
    Liu, Bo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (12) : 2697 - 2699
  • [6] Gold/Lewis Acid Catalyzed Cycloisomerization/Diastereoselective [3+2] Cycloaddition Cascade: Synthesis of Diverse Nitrogen-Containing Spiro Heterocycles
    Wang, Bin
    Liang, Man
    Tang, Jian
    Deng, Yuting
    Zhao, Jinhong
    Sun, Hao
    Tung, Chen-Ho
    Jia, Jiong
    Xu, Zhenghu
    ORGANIC LETTERS, 2016, 18 (18) : 4614 - 4617
  • [7] Synthesis of Polycyclic Nitrogen Heterocycles via Cascade Pd-Catalyzed Alkene Carboamination/Diels-Alder Reactions
    White, Derick R.
    Wolfe, John P.
    ORGANIC LETTERS, 2015, 17 (10) : 2378 - 2381
  • [8] One-Pot Cascade Synthesis of Fused Nitrogen-Containing Heterocycles in Aqueous Media - Utility of N-Protective Groups in Intramolecular Diels-Alder Reaction of Furan
    Demircan, Aydin
    Kandemir, Muhammet K.
    Colak, Medine
    Karaarslan, Muhsin
    SYNTHESIS-STUTTGART, 2016, 48 (17): : 2873 - 2880
  • [9] Highly Selective Synthesis of Seven-Membered Azaspiro Compounds by a Rh(I)-Catalyzed Cycloisomerization/Diels-Alder Cascade of 1,5-Bisallenes
    Vila, Jordi
    Sola, Miquel
    Pla-Quintana, Anna
    Roglans, Anna
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (08): : 5279 - 5286
  • [10] Gold-catalyzed synthesis of oxygen- and nitrogen-containing heterocycles from alkynyl ethers: Application to the total synthesis of andrachcinidine
    Jung, Hyung Hoon
    Floreancig, Paul E.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19): : 7359 - 7366
123