Novel synthesis of highly functionalized cyclopentane derivatives via [3+2] cycloaddition reactions of donor-acceptor cyclopropanes and (E)-3-aryl-2-cyanoacrylates

被引：10
作者：
Dai, Chenlu [1 ]
Li, Mingshuang [1 ]
Chen, Mengjun [1 ]
Luo, Naili [1 ]
Wang, Cunde [1 ]
机构：
[1] Yangzhou Univ, Sch Chem & Chem Engn, 180 Siwangting St, Yangzhou 225002, Jiangsu, Peoples R China
来源：
JOURNAL OF CHEMICAL RESEARCH | 2019年 / 43卷 / 1-2期
基金：
中国国家自然科学基金;
关键词：
1,8-diazabicyclo[5.4.0]undec-7-ene; 3+2] cycloaddition reaction; donor-acceptor cyclopropane; (E)-3-aryl-2-cyanoacrylate; highly functionalized cyclopentane; EFFICIENT STRATEGY; CARBON; CONSTRUCTION; BEARING; ACID;
D O I：
10.1177/1747519819831883
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient [3 + 2] cycloaddition reaction of cyanocyclopropanecarbonates and (E)-3-aryl-2-cyanoacrylates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene for the synthesis of highly functionalized cyclopentane derivatives in moderate to good yields (79%-87%) was developed. The structures of two typical products were confirmed by X-ray crystallography.
引用
收藏
页码：43 / 49
页数：7
相关论文
共 50 条
[21]   A novel type of donor-acceptor cyclopropane with fluorine as the donor: (3+2)-cycloadditions with carbonyls [J].
Liu, Haidong ;
Tian, Lifang ;
Wang, Hui ;
Li, Zhi-Qiang ;
Zhang, Chi ;
Xue, Fei ;
Feng, Chao .
CHEMICAL SCIENCE, 2022, 13 (09) :2686-2691
[22]   Enantioselective (3+2) Annulation of Donor-Acceptor Cyclopropanes with Aldehydes and Ketones Catalyzed by Brønsted Bases [J].
Obregon, Erlaitz B. ;
Rost, Louise G. ;
Kocemba, Ida R. ;
Kristensen, Anne ;
McLeod, David A. ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (42)
[23]   Lewis and Bronsted Acid Induced (3+2)-Annulation of Donor-Acceptor Cyclopropanes to Alkynes: Indene Assembly [J].
Rakhmankulov, Eduard R. ;
Ivanov, Konstantin L. ;
Budynina, Ekaterina M. ;
Ivanova, Olga A. ;
Chagarovskiy, Alexey O. ;
Skvortsov, Dmitriy A. ;
Latyshev, Gennadij V. ;
Trushkov, Igor V. ;
Melnikov, Mikhail Ya .
ORGANIC LETTERS, 2015, 17 (04) :770-773
[24]   Copper Catalyzed [3+2] Annulation of Indoles with 1,1,2,2-Tetrasubstituted Donor-Acceptor Cyclopropanes [J].
Yan Wen-Guang ;
Wang Pan ;
Wang Lijia ;
Sun Xiu-Li ;
Tang Yong .
ACTA CHIMICA SINICA, 2017, 75 (08) :783-787
[25]   Stereoselective syntheses of functionalized spirocyclopenteneoxindoles via triphenylphosphine-catalyzed [3+2] cycloaddition reactions [J].
Zhou, Qing-Fa ;
Chu, Xue-Ping ;
Ge, Fei-Fei ;
Li, Cheng ;
Lu, Tao .
MOLECULAR DIVERSITY, 2013, 17 (03) :563-571
[26]   Synthesis of dihydrocarbazoles via (4+2) annulation of donor-acceptor cyclopropanes to indoles [J].
Liu, Changhui ;
Zhou, Li ;
Huang, Wenbo ;
Wang, Man ;
Gu, Yanlong .
TETRAHEDRON, 2016, 72 (04) :563-570
[27]   A facile and diastereoselective synthesis of functionalized spirooxindoles via 3+2 cycloaddition reaction [J].
Kathirvelan, D. ;
Haribabu, J. ;
Reddy, B. S. R. .
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2015, 54 (08) :965-971
[28]   Lewis Acid Catalyzed Diastereoselective Cycloaddition Reactions of Donor Acceptor Cyclopropanes and Vinyl Azides: Synthesis of Functionalized Azidocyclopentane and Tetrahydropyridine Derivatives [J].
Dey, Raghunath ;
Banerjee, Prabal .
ORGANIC LETTERS, 2017, 19 (02) :304-307
[29]   [3+3] Annulation via Ring Opening/Cyclization of Donor-Acceptor Cyclopropanes with (Un)symmetrical Ureas: A Quick Access to Highly Functionalized Tetrahydropyrimidinones [J].
Taily, Irshad Maajid ;
Saha, Debarshi ;
Banerjee, Prabal .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (48) :7804-7813
[30]   Catalytic (3+2) annulation of donor-acceptor aminocyclopropane monoesters and indoles [J].
Pirenne, Vincent ;
Robert, Emma G. L. ;
Waser, Jerome .
CHEMICAL SCIENCE, 2021, 12 (25) :8706-8712
12345