New Chiral BINOL-Based Phosphates for Enantioselective [Au(I)]-Catalyzed Dearomatization of β-Naphthols with Allenamides

被引:18
|
作者
Pedrazzani, Riccardo [1 ]
An, Juzeng [1 ]
Monari, Magda [1 ]
Bandini, Marco [1 ,2 ]
机构
[1] Univ Bologna, Alma Mater Studiorum, Dipartimento Chim Giacomo Ciamician, Via SeImi 2, I-40126 Bologna, Italy
[2] Consorzio CINMPIS, Via Selmi 2, I-40126 Bologna, Italy
关键词
Asymmetric catalysis; Dearomatization; Homogeneous catalysis; Gold; Chiral counterion; GOLD-CATALYZED DEAROMATIZATION; INTERMOLECULAR ARYLATIVE DEAROMATIZATION; ASYMMETRIC DEAROMATIZATION; INTRAMOLECULAR DEAROMATIZATION; RECENT PROGRESS; INDOLES; PHENOL; ANIONS; FUNCTIONALIZATION; ACTIVATION;
D O I
10.1002/ejoc.202100166
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New chiral BINOL-based phosphate counterions have been synthesized, fully characterized, and employed in the enantioselective gold-catalyzed dearomatization of beta-naphthols with allenamides. A range of densely functionalized C1-allylated naphthalenones were realized under mild conditions and high levels of chemo-, regio- and stereoselectivity (ee up to 95 %).
引用
收藏
页码:1732 / 1736
页数:5
相关论文
共 44 条
  • [41] Enantioselective catalyst based on chiral terpyridine:: Synthesis of new C1 and C2 symmetric 2,2′:6′,2"-terpyridine ligands and copper-catalyzed enantioselective cyclopropanation of alkenes.
    Kwong, HL
    Lee, WS
    Wong, WL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U202 - U202
  • [42] Enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides using a chiral ferrocene-based phosphine-phosphoramidite ligand having a stereogenic P-center
    Yu, Sai-Bo
    Hu, Xiang-Ping
    Deng, Jun
    Wang, Dao-Yong
    Duan, Zheng-Chao
    Zheng, Zhuo
    TETRAHEDRON-ASYMMETRY, 2009, 20 (05) : 621 - 625
  • [43] Rh(I)-Catalyzed Enantioselective Arylation of Cyclic N-Sulfonyl Diketimines Using Planar-Chiral Phosphine-Olefin Ligands Based on a (Cyclopentadienyl)manganese(I) Scaffold with a Highly Fluorinated Aryl Phosphino Group
    Shimamoto, Ryosuke
    Tsurusaki, Akihiro
    Kamikawa, Ken
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (12): : 7882 - 7887
  • [44] New phosphoramidite and phosphito-N chiral ligands based on 8-substituted quinolines and (S)-binaphthol;: applications in the Cu-catalyzed enantioselective conjugate addition of diethylzinc to 2-cyclohexen-1-one
    Arena, CG
    Calabrò, G
    Franciò, G
    Faraone, F
    TETRAHEDRON-ASYMMETRY, 2000, 11 (11) : 2387 - 2392