Six-Membered Cyclic Nitronates as 1,3-Dipoles in Formal [3+3]-Cycloaddition with Donor-Acceptor Cyclopropanes. Synthesis of New Type of Bicyclic Nitrosoacetals

被引：66
|
作者：
Gorbacheva, Evgenia O. [1 ,2 ]
Tabolin, Andrey A. [1 ]
Novikov, Roman A. [1 ]
Khomutova, Yulia A. [1 ]
Nelyubina, Yulia V. [3 ]
Tomilov, Yury V. [1 ]
Ioffe, Sema L. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, Moscow 125047, Russia
[3] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 02期
基金：
俄罗斯基础研究基金会;
关键词：
DIVERSITY-ORIENTED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIPOLAR CYCLOADDITION; 3+2 ANNULATION; TANDEM INTER; NITROALKENES; TETRAHYDRO-1,2-OXAZINES; AMINOCYCLOPROPANES; ALDEHYDES;
D O I：
10.1021/ol303292c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first formal [3 + 3]-cycloaddition of nitronates with donor-acceptor cyclopropanes is reported. The reaction is catalyzed by ytterbium trifluoromethanesulfonate and leads to hitherto unknown bicyclic nitrosoacetals, possessing two annelated six-membered rings.
引用
收藏
页码：350 / 353
页数：4
相关论文
共 21 条
  • [1] (3+3)-Cyclodimerization of Donor-Acceptor Cyclopropanes. Three Routes to Six-Membered Rings
    Ivanova, Olga A.
    Budynina, Ekaterina M.
    Chagarovskiy, Alexey O.
    Trushkov, Igor V.
    Melnikov, Mikhail Ya.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21): : 8852 - 8868
  • [2] Lewis Acid/Rhodium-Catalyzed Formal [3+3]-Cycloaddition of Enoldiazoacetates with Donor-Acceptor Cyclopropanes
    Cheng, Qing-Qing
    Qian, Yu
    Zavalij, Peter Y.
    Doyle, Michael P.
    ORGANIC LETTERS, 2015, 17 (14) : 3568 - 3571
  • [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] Organocatalytic Activation of Donor-Acceptor Cyclopropanes: A Tandem (3+3)-Cycloaddition/Aryl Migration toward the Synthesis of Enantioenriched Tetrahydropyridazines
    Hazra, Arijit
    Dey, Raghunath
    Kushwaha, Apoorv
    Kumar, T. J. Dhilip
    Banerjee, Prabal
    ORGANIC LETTERS, 2023, 25 (29) : 5470 - 5475
  • [5] Stereoretentive Catalytic [3+2]/[3+3]-Cycloaddition of Nonracemic Donor-Acceptor Cyclopropanes: Synthesis of Substituted Pyrrolidines and 1,2-Oxazinanes
    Doyle, Michael P.
    Bao, Ming
    ORGANIC LETTERS, 2023, : 3029 - 3033
  • [6] Accessing substituted pyrrolidines via formal [3+2] cycloaddition of 1,3,5-triazinanes and donor-acceptor cyclopropanes
    Chu, Zhi-Yao
    Li, Na
    Liang, Dan
    Li, Zheng-Hui
    Zheng, Yong-Sheng
    Liu, Ji-Kai
    TETRAHEDRON LETTERS, 2018, 59 (08) : 715 - 718
  • [7] K2CO3-Promoted Formal [3+3]-Cycloaddition of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Knoevenagel Adducts
    Yang, Guosheng
    Li, Sicheng
    Wang, Qiumi
    Chen, Huabao
    Yang, Chunping
    Yin, Zhongqiong
    Song, Xu
    Zhang, Li
    Lu, Cuifen
    Yue, Guizhou
    MOLECULES, 2023, 28 (03):
  • [8] Four-Membered Cycle Formation Challenge: GaCl3-Promoted Formal [2+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Bicyclobutylidene
    Zotova, Maria A.
    Novikov, Roman A.
    Volodin, Alexander D.
    Korlyukov, Alexander A.
    Tkachev, Yaroslav V.
    Korolev, Victor A.
    Tomilov, Yury V.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (26) : 4207 - 4214
  • [9] Donor-acceptor cyclopropanes as three-carbon components in a [4+3] cycloaddition reaction with 1,3-diphenylisobenzofuran
    Ivanova, Olga A.
    Budynina, Ekaterina M.
    Grishin, Yuri K.
    Trushkov, Igor V.
    Verteletskii, Pavel V.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) : 1107 - 1110
  • [10] One-Pot Synthesis of Cycloocta[b]indole Through Formal [5+3] Cycloaddition Using Donor-Acceptor Cyclopropanes
    Okabe, Akito
    Harada, Shinji
    Takeda, Takuya
    Nishida, Atsushi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (24) : 3916 - 3920
123