Silver-catalyzed cyclopropanation of alkenes with alkynyl N-nosylhydrazones leading to alkynyl cyclopropanes

被引:12
作者
Ning, Yongquan [1 ]
Huo, Mengtian [1 ]
Wu, Lizuo [1 ]
Bi, Xihe [1 ,2 ]
机构
[1] Northeast Normal Univ, Dept Chem, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
TERMINAL ALKYNES; RING; INSERTION; BONDS; ALKYNYLCYCLOPROPANES; DERIVATIVES; COMPLEXES; CARBENES; ALLENES; SI;
D O I
10.1039/d2cc00099g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Here, a novel method for the stereoselective synthesis of alkynyl cyclopropanes, by the silver-catalyzed alkynylcyclopropanation of alkenes using alkynyl N-nosylhydrazones as alkynyl carbene precursors, is reported. This method provides a straightforward and powerful approach for preparing various alkynyl cyclopropanes in high yield with excellent stereoselectivities. In addition, the practicality of this method was demonstrated by gram-scale synthesis and late-stage modification of bioactive molecules.
引用
收藏
页码:3485 / 3488
页数:4
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  • [1] Gold-Catalyzed Rearrangements: Reaction Pathways Using 1-Alkenyl-2-alkynylcyclopropane Substrates
    Barluenga, Jose
    Tudela, Eva
    Vicente, Ruben
    Ballesteros, Alfredo
    Tomas, Miguel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) : 2107 - 2110
  • [2] Alkynylcyclopropanes from Terminal Alkynes through Consecutive Coupling to Fischer Carbene Complexes and Selective Propargylene Transfer
    Barluenga, Jose
    Tudela, Eva
    Vicente, Ruben
    Ballesteros, Alfredo
    Tomas, Miguel
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) : 2349 - 2352
  • [3] Total synthesis and structural revision of callipeltoside C
    Carpenter, Joseph
    Northrup, Alan B.
    Chung, deMichael
    Wiener, John J. M.
    Kim, Sung-Gon
    MacMillan, David W. C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) : 3568 - 3572
  • [4] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations
    Cavitt, Marchello A.
    Phun, Lien H.
    France, Stefan
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) : 804 - 818
  • [5] Synthesis of Enantioenriched Allenes from 1,1-Cyclopropanediesters
    Cerat, Pascal
    Gritsch, Philipp J.
    Goudreau, Sebastien R.
    Charette, Andre B.
    [J]. ORGANIC LETTERS, 2010, 12 (03) : 564 - 567
  • [6] Regio- and Diastereoselective Copper-Catalyzed Carbomagnesiation for the Synthesis of Penta- and Hexa-Substituted Cyclopropanes
    Cohen, Yair
    Augustin, Andre U.
    Levy, Laura
    Jones, Peter G.
    Werz, Daniel B.
    Marek, Ilan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (21) : 11804 - 11808
  • [7] Borane-Catalyzed Stereoselective C-H Insertion, Cyclopropanation, and Ring-Opening Reactions
    Dasgupta, Ayan
    Babaahmadi, Rasool
    Slater, Ben
    Yates, Brian F.
    Ariafard, Alireza
    Melen, Rebecca L.
    [J]. CHEM, 2020, 6 (09): : 2364 - 2381
  • [8] Asymmetric synthesis of 1-alkynylcyclopropane-1-carboxylates
    Davies, HML
    Boebel, TA
    [J]. TETRAHEDRON LETTERS, 2000, 41 (43) : 8189 - 8192
  • [9] Pd-Catalyzed Enantioselective Hydroalkynylation of Cyclopropenes
    Dian, Longyang
    Marek, Ilan
    [J]. ACS CATALYSIS, 2020, 10 (02) : 1289 - 1293
  • [10] Cyclopropanation Strategies in Recent Total Syntheses
    Ebner, Christian
    Carreira, Erick M.
    [J]. CHEMICAL REVIEWS, 2017, 117 (18) : 11651 - 11679