Proline-mediated enantioselective construction of tetrahydropyridines via a cascade Mannich-Type/Intramolecular Cyclization reaction

被引:59
|
作者
Han, Rong-Gang [1 ]
Wang, Yao [1 ]
Li, Yu-Ye [1 ]
Xu, Peng-Fei [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
cascade reactions; imines; Mannich-type; reaction; organocatalysis; tetrahydropyridines;
D O I
10.1002/adsc.200800253
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A highly diastereo- and enantioselective synthesis of 2,3-disubstituted tetrahydropyridines was accomplished via a proline-mediated cascade Mannich-type/intramolecular cyclization reaction from preformed N-PMP (p-methoxyphenyl) aldimines and inexpensive aqueous tetrahydro-2Hpyran-2,6-diol.
引用
收藏
页码:1474 / 1478
页数:5
相关论文
共 50 条
  • [11] Synthesis of novel germanium compounds by intramolecular catalytical Mannich-type reaction
    Zhang, ZB
    He, DY
    Zhang, CX
    Chi, GC
    Xu, XH
    Chen, RY
    MAIN GROUP METAL CHEMISTRY, 1997, 20 (06): : 361 - 365
  • [12] Enantioselective Synthesis of Difluoroalkylated Isoindolinones via Chiral Spirocyclic Phosphoric Acid Catalyzed Mannich-Type Reaction
    Wang, Lei
    Zhong, Jialing
    Lin, Xufeng
    SYNLETT, 2021, 32 (04) : 417 - 422
  • [13] Enantioselective Construction of Bispirooxindoles via Squaramide-Catalysed Cascade Michael/Cyclization Reaction
    Zhao, Bo-Liang
    Lin, Ye
    Du, Da-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (14) : 3387 - 3393
  • [14] Formal Synthesis of Ezetimibe Using a Proline-mediated, Asymmetric, Three-component Mannich Reaction
    Shimasaki, Yasuharu
    Koshino, Seitaro
    Hayashi, Yujiro
    CHEMISTRY LETTERS, 2016, 45 (01) : 30 - 32
  • [15] Concise Construction of Sarain A Core According to a Biosynthetic Proposal: Cyclization through an Intramolecular Mannich-type Reaction Involving an Endocyclic N-Acyliminium ion
    Peixoto, Sabrina
    Martin, Marie-Therese
    Crich, David
    Delpech, Bernard
    Marazano, Christian
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (36) : 9907 - 9910
  • [16] An asymmetric oxidative cyclization/Mannich-type addition cascade reaction for direct access to chiral pyrrolidin-3-ones
    Zhou, Su
    Xie, Xiongda
    Xu, Xinxin
    Dong, Shanliang
    Hu, Wenhao
    Xu, Xinfang
    CHEMICAL COMMUNICATIONS, 2021, 57 (91) : 12171 - 12174
  • [17] One-Pot Catalytic Enantioselective Synthesis of Tetrahydropyridines via a Nitro-Mannich/Hydroamination Cascade
    Barber, David M.
    Sanganee, Hitesh J.
    Dixon, Darren J.
    ORGANIC LETTERS, 2012, 14 (20) : 5290 - 5293
  • [18] Aluminium Phosphate Mediated Three-Component Mannich-Type Reaction
    Srinivas, K.
    Reddy, P. Pratap
    Jayaprakash, P.
    Dubey, P. K.
    Chakravarthy, A. Kalyan
    ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (01) : 138 - 140
  • [19] Diastereo- and Enantioselective Mannich/Cyclization Cascade Reaction Access to Chiral Benzothiazolopyrimidine Derivatives
    Zhang, Yan
    Yang, Jia-Hui
    Xia, Ying-Qi
    Dong, Lin
    Chen, Fen-Er
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (20) : 6183 - 6186
  • [20] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL
    Akiyama, T
    Saitoh, Y
    Morita, H
    Fuchibe, K
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1523 - 1526