Synthesis of 2-trifluoromethylated 3-pyrrolines/pyrrolidines via [3+2] cycloaddition of azomethine ylides with the participation of 3,3,3-trifluoroalanine

被引:0
|
作者
Liu, Qian [1 ]
Yoshikawa, Isao [1 ]
Kudo, Kazuaki [1 ]
机构
[1] Univ Tokyo, Inst Ind Sci, 4-6-1 Komaba,Meguro Ku, Tokyo 1538505, Japan
关键词
X=Y-ZH SYSTEMS; 1,3-DIPOLAR CYCLOADDITION; DECARBOXYLATIVE ROUTE; ENANTIOSELECTIVE CONSTRUCTION; ASYMMETRIC CONSTRUCTION; POTENTIAL 1,3-DIPOLES; PYRROLIDINES; MECHANISM; FRAMEWORK; PYRROLES;
D O I
10.1016/j.jfluchem.2022.110061
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
2-Trifluoromethylated 3-pyrrolines and pyrrolidines were synthesized via condensation of 3,3,3-trifluoroalanine with carbonyl compounds, decarboxylative for-mation of azomethine ylides, and the subsequent [3+2] cycloaddition with electron deficient alkynes and alkenes. The reaction proceeded under mild conditions to give the adducts in moderate to good yields. The product 3-pyrroline was successfully converted to the corresponding pyrrole upon treatment with o-iodoxybenzoic acid.
引用
收藏
页数:8
相关论文
共 50 条
  • [1] A SIMPLE SYNTHESIS OF 3,3,3-TRIFLUOROALANINE
    WEYGAND, F
    STEGLICH, W
    FRAUNBERGER, F
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (09) : 808 - +
  • [2] NEW EFFICIENT SYNTHESIS OF 3,3,3-TRIFLUOROALANINE, 2-DEUTERO-3,3,3-TRIFLUOROALANINE AND THEIR N-PROTECTED DERIVATIVES
    BURGER, K
    HOSS, E
    GAA, K
    [J]. CHEMIKER-ZEITUNG, 1989, 113 (7-8): : 243 - 247
  • [3] Synthesis of trifluoromethylated pyrrolidines via decarboxylative [3+2] cycloaddition of non-stabilized N-unsubstituted azomethine ylides
    Zhang, Xiaofeng
    Liu, Miao
    Zhang, Wensheng
    Legris, Marc
    Zhang, Wei
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2017, 204 : 18 - 22
  • [4] [3+2] Cycloaddition of Trifluoromethylated N-Acylhydrazones with Azomethine Ylides: Synthesis of Trifluoromethylated Imidazolidines
    Zhao, Fangxia
    Wang, Ke-Hu
    Wen, Lan
    Zhao, Zhuanxia
    Hu, Yongqin
    Xu, Weigang
    Huang, Danfeng
    Su, Yingpeng
    Wang, Junjiao
    Hu, Yulai
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (07) : 1036 - 1039
  • [5] NEW SYNTHETIC PATHWAYS TO 3,3,3-TRIFLUOROALANINE, 2-DEUTERO-3,3,3-TRIFLUOROALANINE AND THEIR DERIVATIVES
    BURGER, K
    HOSS, E
    GAA, K
    SEWALD, N
    SCHIERLINGER, C
    [J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1991, 46 (03): : 361 - 384
  • [6] A convenient synthesis of 3,3,3-trifluoroalanine derivatives
    A. Yu. Aksinenko
    A. N. Pushin
    V. B. Sokolov
    [J]. Russian Chemical Bulletin, 2002, 51 : 2136 - 2138
  • [7] SYNTHESIS OF 3,3,3-TRIFLUOROALANINE AND OF 3,3,3-TRIFLUOROALANYL PEPTIDES
    WEYGAND, F
    STEGLICH, W
    OETTMEIE.W
    MAIERHOF.A
    LOY, RS
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (06) : 600 - &
  • [8] A convenient synthesis of 3,3,3-trifluoroalanine derivatives
    Aksinenko, AY
    Pushin, AN
    Sokolov, VB
    [J]. RUSSIAN CHEMICAL BULLETIN, 2002, 51 (11) : 2136 - 2138
  • [9] SYNTHESIS OF 3,3,3-TRIFLUOROALANINE FROM HEXAFLUOROACETONE
    BURGER, K
    HUBL, D
    GERTITSCHKE, P
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1985, 27 (03) : 327 - 332
  • [10] Synthesis of muramyl dipeptide analogs by incorporation of 3,3,3-trifluoroalanine
    Wang, ZF
    Xu, JC
    [J]. CHINESE CHEMICAL LETTERS, 2000, 11 (04) : 297 - 300