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
  • [31] 1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts
    Li, Qiang-Qiang
    Hamamoto, Yosuke
    Tan, Cheryl Cai Hui
    Sato, Hiroyasu
    Ito, Shingo
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (15) : 4128 - 4134
  • [32] Synthesis of Novel Trispiroheterocycles through 1,3-Dipolar Cycloaddition of Azomethine Ylides and Nitrile Oxide
    Li Xiaofang
    Yu Xianyong
    Yi Pinggui
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (03) : 434 - 438
  • [33] Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides
    Adrio, Javier
    Carretero, Juan C.
    CHEMICAL COMMUNICATIONS, 2019, 55 (80) : 11979 - 11991
  • [34] Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with α,β-Unsaturated Ketones
    Hernandez-Toribio, Jorge
    Gomez Arrayas, Ramon
    Martin-Matute, Belen
    Carretero, Juan C.
    ORGANIC LETTERS, 2009, 11 (02) : 393 - 396
  • [35] 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides and Alkynylbenziodoxoles for Synthesis of Functional Dibenzoullazines
    Han, Hui
    Goh, Glen Wee Zhuan
    Li, Yongxin
    Yoshikai, Naohiko
    Ito, Shingo
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (10) : 1079 - 1083
  • [36] 1,3-Dipolar cycloaddition of fluorinated azomethine ylides at the C=N bond
    Novikov, MS
    Khlebnikov, AR
    Egarmin, MA
    Kopf, J
    Kostikov, RR
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (10) : 1493 - 1499
  • [37] Synthesis of Pyrrole-Fused Corannulenes: 1,3-Dipolar Cycloaddition of Azomethine Ylides to Corannulene
    Tokimaru, Yuki
    Ito, Shingo
    Nozaki, Kyoko
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) : 15560 - 15564
  • [38] Synthesis of π-Extended Imidazoles by 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides with Nitriles
    Li, Qiang-Qiang
    Ochiai, Kotaro
    Lee, Cherie-Anne
    Ito, Shingo
    ORGANIC LETTERS, 2020, 22 (15) : 6132 - 6137
  • [39] Expeditious Synthesis of Trifluoromethylated Heterocycles: Noncatalytic 1,3-Dipolar Cyclization of Azomethine Imines with (α-Trifluoromethyl)acrylates
    Ogawa, Shinichi
    Nishimine, Takayuki
    Tokunaga, Etsuko
    Shibata, Norio
    SYNTHESIS-STUTTGART, 2010, (19): : 3274 - 3281
  • [40] Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1,3-Dipolar Cycloaddition of Azomethine Ylides to Cyclopropenes
    Filatov, Alexander S.
    Knyazev, Nickolay A.
    Shmakov, Stanislav V.
    Bogdanov, Alexey A.
    Ryazantsev, Mikhail N.
    Shtyrov, Andrey A.
    Starova, Galina L.
    Molchanov, Alexander P.
    Larina, Anna G.
    Boitsov, Vitali M.
    Stepakov, Alexander V.
    SYNTHESIS-STUTTGART, 2019, 51 (03): : 713 - 729
12345