One-pot synthesis and theoretical calculation for trifluoromethylated pyrrolizidines by 1,3-dipolar cycloaddition with azomethine ylides and β-trifluoromethyl acrylamides

被引：15
|
作者：
Toma, Yoshiki [1 ]
Kunigami, Masataka [1 ]
Watanabe, K-jiro [1 ]
Higashi, Masahiro [1 ]
Arimitsu, Satoru [1 ]
机构：
[1] Univ Ryukyus, Dept Chem Biol & Marine Sci, 1 Senbaru, Nishihara, Okinawa 9030123, Japan
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2016年 / 189卷
关键词：
Trifluoromethylated pyrrolizidines; 1,3-dipolar cycloaddition; beta-Trifluoromethyl acrylamides; Diastereoselective; DFT calculation; MEDICINAL CHEMISTRY; IONIC-SOLUTIONS; PROLINE; FLUORINE; REGIOSELECTIVITY; REACTIVITY; ACCESS; DFT;
D O I：
10.1016/j.jfluchem.2016.07.013
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The reaction with beta-trifluoromethyl acrylamide 3e and azomethine ylides generated from L-proline and several aldehydes provided the corresponding trifluoromethylated pyrrolizidines with excellent diastereoselectivity (>20/1) in all cases and moderate regioselectivity (up to 1/5.9). A DFT calculation was also examined to reveal the origin of these stereoselectivities. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码：22 / 32
页数：11
相关论文
共 50 条
  • [21] Direct synthesis of pyrroles via 1,3-dipolar cycloaddition of azomethine ylides with ynones
    Wang, Zheng
    Shi, Ying
    Luo, Xiaoyan
    Han, De-Man
    Deng, Wei-Ping
    NEW JOURNAL OF CHEMISTRY, 2013, 37 (06) : 1742 - 1745
  • [22] Diastereoselective 1,3-dipolar cycloaddition of cyclopropenes to acenaphthenequinone azomethine ylides
    Stepakov, Alexander, V
    Pronina, Yulia A.
    Filatov, Alexander S.
    Selivanov, Stanislav I.
    Kornev, Anton A.
    Kryukova, Mariya A.
    Ponyaev, Alexander I.
    Boitsov, Vitali M.
    TETRAHEDRON, 2024, 151
  • [23] 1,3-Dipolar cycloaddition reactions of azomethine ylides with aromatic dipolarophiles
    Ryan, John H.
    ARKIVOC, 2015, : 160 - 183
  • [24] Unprecedented 1,3-dipolar cycloaddition of azomethine ylides to ester carbonyl
    Novikov, MS
    Voznyi, IV
    Khlebnikov, AF
    Kopf, J
    Kostikov, RR
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14): : 1628 - 1630
  • [25] Chiral oxazolines in 1,3-dipolar cycloaddition reactions of azomethine ylides
    Husinec, S
    Savic, V
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 1998, 63 (12) : 921 - 930
  • [26] DIASTEREOFACIAL SELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES
    DEPREZ, P
    ROUDEN, J
    CHIARONI, A
    RICHE, C
    ROYER, J
    HUSSON, HP
    TETRAHEDRON LETTERS, 1991, 32 (51) : 7531 - 7534
  • [27] 1,3-DIPOLAR CYCLO-ADDITIONS OF AZOMETHINE YLIDES WITH DIPOLAROPHILES .2. SYNTHESIS OF PYRROLIZIDINES
    ORSINI, F
    PELIZZONI, F
    FORTE, M
    SISTI, M
    MERATI, F
    GARIBOLDI, P
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (06) : 1665 - 1673
  • [28] One-Step Method for the Synthesis of Nitroisoindoles via 1,3-Dipolar Cycloaddition of Azomethine Ylides to Polynitrobenzenes
    Starosotnikov, Alexey M.
    Bastrakov, Maxim A.
    Kachala, Vadim V.
    Belyakov, Pavel A.
    Fedyanin, Ivan V.
    Shevelev, Svyatoslav A.
    SYNLETT, 2012, (16) : 2400 - 2404
  • [29] Theoretical study of the 1,3-dipolar cycloaddition reactions of azomethine ylides. A DFT study of reaction between trifluoromethyl thiomethyl azomethine ylide and acronitrile
    Domingo, LR
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11): : 3922 - 3929
  • [30] Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
    Ponce, Alberto
    Alonso, Ines
    Adrio, Javier
    Carretero, Juan C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (14) : 4952 - 4959
12345