Stereoselectivity in the double reductive alkylation of pyrroles:: synthesis of cis-3,4-disubstituted pyrrolidines

被引:10
|
作者
Donohoe, TJ
Harji, RR
Cousins, RPC
机构
[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1039/a809193e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The preparation and Birch reduction of a 1,3,4-tri-substituted pyrrole is described: the heterocycle is loaded with electron-withdrawing groups and undergoes a double reductive alkylation reaction to yield cis-3,4-disubstituted pyrrolidines.
引用
收藏
页码:141 / 142
页数:2
相关论文
共 50 条
  • [1] Enantioselective biocatalytic desymmetrization for synthesis of enantiopure cis-3,4-disubstituted pyrrolidines
    Hu, Hui-Juan
    Wang, Qi-Qiang
    Wang, De-Xian
    Ao, Yu-Fei
    GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (03): : 324 - 327
  • [2] A NOVEL SYNTHESIS OF CIS-3,4-DISUBSTITUTED CYCLOPENTANONES
    SAKAI, K
    ISHIGURO, Y
    FUNAKOSHI, K
    UENO, K
    SUEMUNE, H
    TETRAHEDRON LETTERS, 1984, 25 (09) : 961 - 964
  • [3] Asymmetric synthesis of cis-3,4-disubstituted β-sultams
    Enders, D
    Moll, A
    SYNTHESIS-STUTTGART, 2005, (11): : 1807 - 1816
  • [4] HIGHLY SELECTIVE SYN ACYCLIC HOMOALDOL CHEMISTRY - SYNTHESIS OF CIS-3,4-DISUBSTITUTED BUTYROLACTONES
    MCKENZIE, JR
    LINDERMAN, RJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 46 - ORGN
  • [5] HIGHLY SELECTIVE SYN ACYCLIC HOMOALDOL CHEMISTRY - SYNTHESIS OF CIS-3,4-DISUBSTITUTED BUTYROLACTONES
    LINDERMAN, RJ
    MCKENZIE, JR
    TETRAHEDRON LETTERS, 1988, 29 (32) : 3911 - 3914
  • [6] A simple strategy for the synthesis of 3,4-disubstituted pyrroles
    Padmavathi, V
    Reddy, BJM
    Sarma, MR
    Thriveni, P
    JOURNAL OF CHEMICAL RESEARCH, 2004, (01) : 79 - 80
  • [7] Synthesis of 3,4-Disubstituted Pyrroles. A Review
    Leeper, Finian J.
    Kelly, James M.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2013, 45 (03) : 171 - 210
  • [8] Synthesis of Chiral 3,4-Disubstituted Pyrrolidines with Antibacterial Properties
    Rodriguez, Lenka
    Fisera, Roman
    Gaalova, Barbora
    Koci, Kamila
    Bujdakova, Helena
    Meciarova, Maria
    Gorova, Renata
    Jurdakova, Helena
    Sebesta, Radovan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (17) : 2565 - 2575
  • [9] Lithium hydroxide mediated synthesis of 3,4-disubstituted pyrroles
    Sharma, Ratnesh
    Kumar, Kapil
    Chouhan, Mangilal
    Grover, Vikas
    Nair, Vipin A.
    RSC ADVANCES, 2013, 3 (34) : 14521 - 14527
  • [10] A CONVENIENT METHOD FOR THE SYNTHESIS OF UNSYMMETRICAL 3,4-DISUBSTITUTED PYRROLES
    SHUM, PW
    KOZIKOWSKI, AP
    TETRAHEDRON LETTERS, 1990, 31 (47) : 6785 - 6788