Enantioselective construction of lactone[2,3-b]piperidine skeletons via organocatalytic tandem reactions

被引:37
|
作者
He, Zhao-Quan [1 ,2 ]
Han, Bo [2 ]
Li, Rui [1 ]
Wu, Li [2 ]
Chen, Ying-Chun [1 ,2 ]
机构
[1] Sichuan Univ, State Key Lab Biotherapy, W China Hosp, Chengdu 610041, Peoples R China
[2] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Dept Med Chem, W China Sch Pharm,Educ Minist, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
DIELS-ALDER REACTION; IODOXYBENZOIC ACID IBX; ALPHA; BETA-UNSATURATED ALDEHYDES; MICHAEL ADDITION; DOMINO REACTIONS; STEREOCENTERS; OXIDATION; ASPIDOPHYTINE; HAPLOPHYTINE; CHEMISTRY;
D O I
10.1039/b922053d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly enantioselective construction of delta- and gamma-lactone[2,3-b] piperidine skeletons was accomplished by tandem aza-Diels-Alder reaction-hemiacetal formation-oxidation from N-Tos-1-aza-1,3-butadienes and aliphatic dialdehydes.
引用
收藏
页码:755 / 757
页数:3
相关论文
共 50 条
  • [1] Enantioselective Organocatalytic Domino Michael/Aldol Reactions: An Efficient Procedure for the Stereocontrolled Construction of 2H-Thiopyrano[2,3-b]quinoline Scaffolds
    Wu, Lulu
    Wang, Youming
    Song, Haibin
    Tang, Liangfu
    Zhou, Zhenghong
    Tang, Chuchi
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (09) : 2204 - 2210
  • [2] Diastereo- and Enantioselective Construction of Dihydroisocoumarin-Based Spirooxindole Frameworks via Organocatalytic Tandem Reactions
    Wu, Jia-Le
    Du, Bai-Xiang
    Zhang, Yu-Chen
    He, Ying-Ying
    Wang, Jing-Yi
    Wu, Ping
    Shi, Feng
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (17) : 2777 - 2790
  • [3] Enantioselective synthesis of 8-membered lactone derivatives via organocatalytic cascade reactions
    Ji, Dong-Sheng
    Zhang, Rui
    Han, Xu-Yan
    Chai, Hai-Long
    Gu, Yucheng
    Hu, Xiu-Qin
    Xu, Peng-Fei
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (10) : 2911 - 2916
  • [4] Organocatalytic asymmetric Friedel-Crafts alkylation/hemiketalization/lactonization cascade reactions: highly enantioselective synthesis of furo[2,3-b]benzofuranones
    Xu, Kunhua
    Chen, Wenming
    Chen, Xu
    Wang, Biao
    Huang, Jun
    Tian, Xu
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (13) : 1679 - 1684
  • [5] Enantioselective Construction of 2,3-Dihydrofuro[2,3-b]quinolines through Supramolecular Hydrogen Bonding Interactions
    Zhong, Fangrui
    Bach, Thorsten
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (42) : 13522 - 13526
  • [6] The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylis-Hillman adduct acetates
    Moghaddam, Firouz Matloubi
    Foroushani, Behzad Koushki
    Sobhani, Maryam
    Masoud, Nazila
    Khodabakhshi, Mohammad Reza
    Weng, Ng Seik
    TETRAHEDRON, 2013, 69 (38) : 8169 - 8173
  • [7] Diverse synthesis of pyrano[2,3-b]indol and dihydropyrano[2,3-b]indol via tunable Lewis bases catalyzed domino reactions
    Liu, Yufen
    Du, Yanlong
    Yu, Aimin
    Qin, Dabin
    Meng, Xiangtai
    TETRAHEDRON, 2015, 71 (40) : 7706 - 7716
  • [8] Tandem Synthesis of Pyrrolo[2,3-b]quinolones via Cadogen-Type Reaction
    Lin, Zhichen
    Hu, Zhongyan
    Zhang, Xin
    Dong, Jinhuan
    Liu, Jian-Biao
    Chen, De-Zhan
    Xu, Xianxiu
    ORGANIC LETTERS, 2017, 19 (19) : 5284 - 5287
  • [9] Cycloaddition reactions of furo[2,3-b]pyrroles
    Sleziak, R
    Krutosíková, A
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1999, 64 (02) : 321 - 328
  • [10] SOME REACTIONS OF NAPHTHO[2,3-B]THIOPHEN
    CARRUTHERS, W
    JOURNAL OF THE CHEMICAL SOCIETY, 1963, (SEP): : 4477 - &