Stereoselective Synthesis of Tetrahydroquinolines Through an Imino-Ene Cyclization Reaction

被引:12
|
作者
Bondalapati, Somasekhar [1 ]
Indukuri, Kiran [1 ]
Ghosh, Priya [1 ]
Saikia, Anil K. [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India
关键词
Synthetic methods; Nitrogen heterocycles; Cyclization; Diastereoselectivity; Lewis acids; ENANTIOSELECTIVE TOTAL-SYNTHESIS; AZA-PRINS-CYCLIZATION; SOLUTION-PHASE; CARBONYL-ENE; SOLID-PHASE; DERIVATIVES; ALKALOIDS; CATALYSIS; HETEROCYCLES; BENZASTATINS;
D O I
10.1002/ejoc.201201363
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tetrahydroquinolines have been efficiently synthesized in good yields with excellent stereoselectivity. The reaction between alpha-allylic anilines and aldehydes proceeds through an imino-ene cyclization that is mediated by boron trifluoride-diethyl ether.
引用
收藏
页码:952 / 956
页数:5
相关论文
共 50 条
  • [31] Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction
    Ghorai, Manas K.
    Das, Subhomoy
    Das, Kalpataru
    Kumar, Amit
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (34) : 9042 - 9049
  • [32] An efficient synthesis of dihydro- and tetrahydropyrans via oxonium-ene cyclization reaction
    Bondalapati, Somasekhar
    Reddy, Udagandla C.
    Saha, Pipas
    Saikia, Anil K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (09) : 3428 - 3438
  • [33] A novel synthesis of α-amino acid derivatives through catalytic, enantioselective ene reactions of α-imino esters
    Drury, WJ
    Ferraris, D
    Cox, C
    Young, B
    Lectka, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) : 11006 - 11007
  • [34] Imino Diels-Alder reactions: One-pot synthesis of tetrahydroquinolines
    Kamble, Vinod T.
    Davane, Bhaskar S.
    Chavan, Sanjay A.
    Muley, Dnyanoba B.
    Atkore, Sandeep T.
    CHINESE CHEMICAL LETTERS, 2010, 21 (03) : 265 - 268
  • [35] Stereoselective Synthesis of Five-Membered Spirooxindoles through Tomita Zipper Cyclization
    Ramachary, D. B.
    Venkaiah, Chintalapudi
    Krishna, Patoju M.
    ORGANIC LETTERS, 2013, 15 (18) : 4714 - 4717
  • [36] Stereoselective synthesis of cyclopentanone-fused benzosultams through Tomita zipper cyclization
    Ramachary, Dhevalapally B.
    Krishna, Patoju M.
    Reddy, T. Prabhakar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (27) : 6413 - 6416
  • [37] Imino Diels-Alder reactions:One-pot synthesis of tetrahydroquinolines
    Vinod T.Kamble
    Bhaskar S.Davane
    Sanjay A.Chavan
    Dnyanoba B.Muley
    Sandeep T.Atkore
    Chinese Chemical Letters, 2010, 21 (03) : 265 - 268
  • [38] On-Demand Selection of the Reaction Path from Imino Diels-Alder to Ene-Type Cyclization: Synthesis of Epiminopyrimido[4,5-b]azepines
    Zhang, Yuewei
    Zhu, Yue
    Zheng, Lianyou
    Zhuo, Lian-Gang
    Yang, Fengzhi
    Dang, Qun
    Yu, Zhi-Xiang
    Bai, Xu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (03) : 660 - 669
  • [39] Ene reactions of alkynes for the stereoselective synthesis of allylamines
    Ofial, AR
    Mayr, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2): : 143 - 145
  • [40] A convergent enantioselective total synthesis of (-)-perhydrohistrionicotoxin with an intramolecular imino ene-type reaction as a key step
    Tanner, D
    Hagberg, L
    TETRAHEDRON, 1998, 54 (27) : 7907 - 7918