Regio- and Stereoselective Copper-Catalyzed Allylation of 1,3-Dicarbonyl Compounds with Terminal Allenes

被引:24
|
作者
Blieck, Remi [1 ]
Abdine, Racha Abed Ali [1 ]
Taillefer, Marc [1 ]
Monnier, Florian [1 ,2 ]
机构
[1] Ecole Natl Super Chim Montpellier, Inst Charles Gerhardt Montpellier, CNRS, UMR 5253,AM2N, 8 Rue Ecole Normale, F-34296 Montpellier 5, France
[2] IUF, 1 Rue Descartes, F-75231 Paris 5, France
关键词
REGIOSELECTIVE ACCESS; HYDROAMINATION; ALKYNES; PRONUCLEOPHILES; HYDROALKOXYLATION; CONSTRUCTION; AMINES; HYDROCARBONATION; ALKOXYALLENES; TERTIARY;
D O I
10.1021/acs.orglett.8b00575
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Simple ligand-free copper systems were found as efficient catalysts for the addition of 1,3-dicarbonyl compounds to N-allenyl derivatives. This highly regio- and stereoselective reaction has been accomplished in the presence of malonates, 1,3-ketoesters, and 1,3-diketones with good to excellent yields under mild conditions. This methodology represents the first allylation of 1,3-dicarbonyl compounds with allenes catalyzed by copper.
引用
收藏
页码:2232 / 2235
页数:4
相关论文
共 50 条
  • [21] Ligand-free copper-catalyzed regio- and stereoselective 1,1-alkylmonofluoroalkylation of terminal alkynes
    Lv, Yunhe
    Pu, Weiya
    Wang, Xiaoxing
    CHEMICAL COMMUNICATIONS, 2020, 56 (85) : 12933 - 12936
  • [22] Metal triflate-catalyzed cationic benzylation and allylation of 1,3-dicarbonyl compounds
    Noji, Masahiro
    Konno, Yosuke
    Ishii, Keitaro
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14): : 5161 - 5167
  • [23] Regio- and Stereoselective Allylation of Anilines with Aryl Allenes in Hexafluoroisopropanol Solvent
    Ghosh, Suman
    Saha, Shib Nath
    Baidya, Mahiuddin
    ORGANIC LETTERS, 2023, 25 (27) : 5073 - 5077
  • [24] Copper-Catalyzed Regio- and Stereoselective Hydrothiolation of Allenamides, Enamides, and Ynamides
    Pages, Lucas
    Bouquin, Maxime
    Jaroschik, Florian
    Monnier, Florian
    Taillefer, Marc
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (02): : 1168 - 1176
  • [25] Regio- and stereoselective copper-catalyzed β-borylation of allenoates by a preactivated diboron
    Thorpe, Steven B.
    Guo, Xi
    Santos, Webster L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [26] Regio- and stereoselective copper-catalyzed β-borylation of allenoates by a preactivated diboron
    Thorpe, Steven B.
    Guo, Xi
    Santos, Webster L.
    CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 424 - 426
  • [27] Copper(II) Triflate Catalyzed Amination of 1,3-Dicarbonyl Compounds
    Thi My Uyen Ton
    Himawan, Fanny
    Chang, Joyce Wei Wei
    Chan, Philip Wai Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (38) : 12020 - 12027
  • [28] Copper-Catalyzed Regio- and Stereoselective O-Arylation of Enolates
    Xu, Ze-Feng
    Cai, Chen-Xin
    Jiang, Min
    Liu, Jin-Tao
    ORGANIC LETTERS, 2014, 16 (13) : 3436 - 3439
  • [29] Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Pyridazinones with Terminal Allenes
    Parveen, Shaista
    Li, Changkun
    Hassan, Abbas
    Breit, Bernhard
    ORGANIC LETTERS, 2017, 19 (09) : 2326 - 2329
  • [30] Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds
    Borduas, Nadine
    Powell, David A.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19): : 7822 - 7825