Modification of chiral monodentate phosphine ligands (MOP) for palladium-catalyzed asymmetric hydrosilylation of cyclic 1,3-dienes

被引:1
|
作者
Hayashi, T [1 ]
Han, JS [1 ]
Takeda, A [1 ]
Tang, J [1 ]
Nohmi, K [1 ]
Mukaide, K [1 ]
Tsuji, H [1 ]
Uozumi, Y [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
allylsilane; asymmetric catalysis; chiral monodentate phosphine ligands; hydrosilylations; palladium;
D O I
10.1002/1615-4169(20010330)343:3<279::AID-ADSC279>3.3.CO;2-X
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Several MOP ligands 5 containing aryl groups at 2' position of (R)-2-(diphenylphosphino)-1,1'-binaphthyl skeleton were prepared and used for palladium-catalyzed asymmetric hydrosilylation of cyclic 1,3-dienes 6 with trichlorosilane. Highest enantioselectivity was observed in the reaction of 1,3-cyclopentadiene (6a) catalyzed by a palladium complex (0.25 mol %) coordinated with (R)-2-(di-phenylphosphino)-2'-(3,5-dimethyl-4-methoxyphenyl)-1,1'-binaphthyl (5f), which gave (S)-3-(trichlorosilyl)cyclopentene of 90% ee.
引用
收藏
页码:279 / 283
页数:5
相关论文
共 50 条
  • [1] Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes
    Shen, Hong-Cheng
    Wu, Yu-Feng
    Zhang, Ying
    Fan, Lian-Feng
    Han, Zhi-Yong
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) : 2372 - 2376
  • [2] Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides
    Li, Ming-Ming
    Cheng, Lei
    Xiao, Li-Jun
    Xie, Jian-Hua
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) : 2948 - 2951
  • [3] Palladium-catalyzed hydrophosphorylation of 1,3-dienes leading to allylphosphonates
    Mirzaei, F
    Han, LB
    Tanaka, M
    TETRAHEDRON LETTERS, 2001, 42 (02) : 297 - 299
  • [4] Palladium-Catalyzed Cyclization Amination of Propargylamine and 1,3-Dienes
    Yao, Biao
    Xiong, Wenfang
    Wu, Wanqing
    Jiang, Huanfeng
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [5] PALLADIUM-CATALYZED ANNULATION OF OXYGEN-SUBSTITUTED 1,3-DIENES
    LAROCK, RC
    GUO, LQ
    SYNLETT, 1995, (05) : 465 - 466
  • [6] Palladium-Catalyzed Elimination/Isomerization of Enol Triflates into 1,3-Dienes
    Crouch, Ian T.
    Dreier, Timothy
    Frantz, Doug E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) : 6128 - 6132
  • [7] Palladium-catalyzed Asymmetric Hydrosilylation of Styrene and Its Derivatives with Chiral Phosphoramidite Ligands Containing Chiral Ferrocenyl Amine
    Park, Hyun-Sub
    Kim, Min Young
    Ahn, Hyo Jin
    Han, Jin Wook
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (06): : 795 - 796
  • [8] Axially chiral monophosphine ligands (MOPs) and their use for palladium-catalyzed asymmetric hydrosilylation of olefins
    Hayashi, T
    CATALYSIS TODAY, 2000, 62 (01) : 3 - 15
  • [9] Palladium-Catalyzed Allylation of Cyclopropyl Acetylenes with Oxindoles to Construct 1,3-Dienes
    Lu, Chuan-Jun
    Yu, Xin
    Chen, Yu-Ting
    Song, Qing-Bao
    Yang, Zhen-Ping
    Wang, Hong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (06) : 680 - 688
  • [10] Palladium-Catalyzed Asymmetric Hydrosilylation of Cyclohexa-1,3-diene with Trichlorosilane by Use of Chiral Phosphoramidite Ligands from 3,3′-Disubstituted 1,1′-Binaphthols
    Park, Hyun-Sub
    Shin, Hye Mi
    Namgung, Suk
    Han, Jin Wook
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (09): : 2613 - 2614