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

页码：43 / 49

页数：7

共 50 条

[1] Lewis Acid-Catalyzed [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and Enamines: Enantioselective Synthesis of Nitrogen-Functionalized Cyclopentane Derivatives
Verma, Kamal
Banerjee, Prabal
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) : 2053 - 2058
[2] (3+2)-Cycloaddition of Donor-Acceptor Cyclopropanes with Selenocyanate: Synthesis of Dihydroselenophenes and Selenophenes
Jacob, Anu
Jones, Peter G.
Werz, Daniel B.
ORGANIC LETTERS, 2020, 22 (21) : 8720 - 8724
[3] Formal [3+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
Budynina, Ekaterina M.
Ivanova, Olga A.
Chagarovskiy, Alexey O.
Grishin, Yuri K.
Trushkov, Igor V.
Melnikov, Mikhail Ya.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24): : 12212 - 12223
[4] Competition of (3+2) annulation and (3+2) cycloaddition in the reaction of alkenes with donor-acceptor cyclopropanes
Volkova, Yu. A.
Boichenko, M. A.
Shorokhov, V. V.
Zhokhov, S. S.
Andreev, I. A.
Ratmanova, N. K.
Trushkov, I. V.
Ivanova, O. A.
RUSSIAN CHEMICAL BULLETIN, 2024, 73 (05) : 1237 - 1252
[5] Novel synthesis of furancarboxylate derivatives via cyclization reactions of (E)-ethyl 3-aryl-2-cyanoacrylates and ethyl glycinate hydrochloride
Luo, Naili
Wang, Shan
Su, Zhenjie
Wang, Cunde
JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (5-6) : 476 - 481
[6] Donor-acceptor cyclopropanes as building blocks in (3+2) annulation reactions
Parsons, Andrew T.
Smith, Austin G.
Johnson, Jeffrey S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[7] Ferrocenyl-substituted tetrahydrothiophenes via formal [3+2]-cycloaddition reactions of ferrocenyl thioketones with donor-acceptor cyclopropanes
Mloston, Grzegorz
Kowalczyk, Mateusz
Augustin, Andre U.
Jones, Peter G.
Werz, Daniel B.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 1288 - 1295
[8] Photoredox Activation of Donor-Acceptor Cyclopropanes: Distonic Radical Cation Reactivity in [3+2] Cycloaddition Reactions
Mondal, Subhashis
Debnath, Saradindu
Lo, Rabindranath
Maity, Soumitra
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (07)
[9] Lewis Acid Catalyzed Formal [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and 1-Azadienes: Synthesis of Imine Functionalized Cyclopentanes and Pyrrolidine Derivatives
Verma, Kamal
Banerjee, Prabal
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (21) : 3848 - 3854
[10] [3+2] Annulation of Donor-Acceptor Cyclopropanes with Vinyl Azides
Kaga, Atsushi
Gandamana, Dhika Aditya
Tamura, Sayako
Demirelli, Mesut
Chiba, Shunsuke
SYNLETT, 2017, 28 (09) : 1091 - 1095

← 1 2 3 4 5 →