Lewis Acid/Rhodium-Catalyzed Formal [3+3]-Cycloaddition of Enoldiazoacetates with Donor-Acceptor Cyclopropanes

被引：59
|
作者：
Cheng, Qing-Qing [1 ]
Qian, Yu [2 ]
Zavalij, Peter Y. [2 ]
Doyle, Michael P. [1 ]
机构：
[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA
[2] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 14期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
ENANTIOSELECTIVE 3+3 CYCLOADDITION; AZOMETHINE IMINES; CARBONYL-COMPOUNDS; ORGANIC-SYNTHESIS; PROPARGYL ESTERS; CONSTRUCTION; 1,1-DIESTERS; DERIVATIVES; ANNULATION; ENAMINES;
D O I：
10.1021/acs.orglett.5b01674
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A formal [8 + 3]-cycloaddition, of enoldiazoacetates with donor acceptor cyclopropanes was realized by the Combination of a Lewis acid-catalyzed diastereoselective [3 + 2]-cycloaddition and a subsequent rhodium-catalyzed chemoselective ring expansion. This tandem transformation provides an efficient approach to highly functionalized cyclohexenes.
引用
收藏
页码：3568 / 3571
页数：4
相关论文
共 50 条
  • [1] One-Pot Au[III]-/Lewis Acid Catalyzed Cycloisomerization of Nitroalkynes and [3+3]Cycloaddition with Donor-Acceptor Cyclopropanes
    Dhote, Pawan S.
    Ramana, Chepuri, V
    [J]. ORGANIC LETTERS, 2019, 21 (16) : 6221 - 6224
  • [2] Lewis Acid Catalyzed [3+3] Annulation of Donor-Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans
    Mondal, Keshab
    Pan, Subhas Chandra
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (03) : 534 - 537
  • [3] (3+3)-Annulation of Donor-Acceptor Cyclopropanes with Diaziridines
    Chagarovskiy, Alexey O.
    Vasin, Vladimir S.
    Kuznetsov, Vladimir V.
    Ivanova, Olga A.
    Rybakov, Victor B.
    Shumsky, Alexey N.
    Makhova, Nina N.
    Trushkov, Igor V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) : 10338 - 10342
  • [4] Lewis Acid Mediated [3+2] and [3+3] Annulations of an Azomethine Imine with Donor-Acceptor Cyclopropanes
    Mandadapu, Raghuramaiah
    Dehade, Amol Satish
    Shete, Shrikant Abhiman
    Montgomery, Mark
    Sikervar, Vikas
    Sonawane, Ravindra
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (16): : 2865 - 2873
  • [5] Lewis Acid Catalyzed (3+2)-Annulations of Donor-Acceptor Cyclopropanes and Ynamides
    Mackay, William D.
    Fistikci, Meryem
    Carris, Ryan M.
    Johnson, Jeffrey S.
    [J]. ORGANIC LETTERS, 2014, 16 (06) : 1626 - 1629
  • [6] Lewis Acid Catalyzed Reactions of Donor-Acceptor Cyclopropanes with Anthracenes
    Ivanova, Olga A.
    Budynina, Ekaterina M.
    Grishin, Yuri K.
    Trushkov, Igor V.
    Verteletskii, Pavel V.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) : 5329 - 5335
  • [7] [3+3]-Cycloaddition of Donor-Acceptor Cyclopropanes with Nitrile Imines Generated in Situ: Access to Tetrahydropyridazines
    Garve, Lennart K. B.
    Petzold, Martin
    Jones, Peter G.
    Werz, Daniel B.
    [J]. ORGANIC LETTERS, 2016, 18 (03) : 564 - 567
  • [8] (3+3)-Annulation of Carbonyl Ylides with Donor-Acceptor Cyclopropanes: Synergistic Dirhodium(II) and Lewis Acid Catalysis
    Petzold, Martin
    Jones, Peter G.
    Werz, Daniel B.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (19) : 6225 - 6229
  • [9] Formal Insertion of Thioketenes into Donor-Acceptor Cyclopropanes by Lewis Acid Catalysis
    Augustin, Andre U.
    Busse, Marius
    Jones, Peter G.
    Werz, Daniel B.
    [J]. ORGANIC LETTERS, 2018, 20 (03) : 820 - 823
  • [10] Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes
    Mloston, Grzegorz
    Kowalczyk, Mateusz
    Augustin, Andre U.
    Jones, Peter G.
    Werz, Daniel B.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (46) : 6250 - 6253
12345