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
  • [31] Copper(I)-catalyzed regio- and diastereoselective intramolecular alkylboration of terminal allenes
    Ozawa, Yu
    Iwamoto, Hiroaki
    Ito, Hajime
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [32] Regio- and Stereoselective Copper-Catalyzed Addition of Aromatic and Aliphatic Thiols to Terminal and Internal Nonactivated Alkynes
    Trostyanskaya, Inna G.
    Beletskaya, Irina P.
    SYNLETT, 2012, (04) : 535 - 540
  • [33] Regio- and Stereoselective Copper-Catalyzed Borylation-Protodeboronation of 1,3-Diynes: Access to (Z)-1,3-Enynes
    Burgio, Ariel L.
    Buchbinder, Nicklas W.
    Santos, Webster L.
    ORGANIC LETTERS, 2023, 25 (15) : 2652 - 2656
  • [34] Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes
    Kato, Kodai
    Hirano, Koji
    Miura, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (22) : 5775 - 5778
  • [35] Cobalt-Catalyzed Regio- and Stereoselective Hydroboration of Allenes
    Li, Can
    Yang, Zheng
    Wang, Lei
    Guo, Yinlong
    Huang, Zheng
    Ma, Shengming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (15) : 6278 - 6283
  • [36] Copper-Catalyzed Regio- and Stereoselective Conjugate Allylation of Electron-Deficient Alkynes with Allylboronates under Mild Conditions
    Yamamoto, Yoshihiko
    Yamada, Satoshi
    Nishiyama, Hisao
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (11) : 3153 - 3156
  • [37] Iodine-catalyzed allylation of 1,3-dicarbonyl compounds with allylic alcohols at room temperature
    Rao, Weidong
    Tay, Adeline Hui Ling
    Goh, Pei Jing
    Choy, Jessica Mun Ling
    Ke, Justin Kaijie
    Chan, Philip Wai Hong
    TETRAHEDRON LETTERS, 2008, 49 (01) : 122 - 126
  • [38] Cobalt(III)-Catalyzed and DMSO-Involved Allylation of 1,3-Dicarbonyl Compounds with Alkenes
    Zhang, Xu
    Xu, Xuefeng
    Shi, Yue
    Wang, Di
    Ding, Yanhua
    Chen, Shuyang
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14352 - 14363
  • [39] Highly efficient copper(II)-catalyzed amination of 1,3-dicarbonyl compounds
    Thi My Uyen Ton
    Chan, Philip Wai Hong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [40] Regio- and stereoselective copper-catalyzed carbozincation reactions of alkynyl sulfoximines and sulfones
    Sklute, Genia
    Bolm, Carsten
    Marek, Ilan
    ORGANIC LETTERS, 2007, 9 (07) : 1259 - 1261