Stereoselective synthesis of sugar allenes and their hydrosilylation catalyzed by biscobaltoctacarbonyl

被引:41
|
作者
Huang, GB [1 ]
Isobe, M [1 ]
机构
[1] Nagoya Univ, Organ Chem Lab, Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan
基金
日本学术振兴会;
关键词
sugar allenes; biscobaltoctacarbonyl; hydrosilylation;
D O I
10.1016/S0040-4020(01)01066-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoselective introduction of allenyl group to glycals has been developed with propargyltrimethylsilane under the catalysis of a Lewis acid to produce largely the a-sugar allenes in good yields. The subsequent hydrosilylations of these sugar allenes were catalyzed by biscobaltoctacarbonyl to obtain the corresponding vinylsilanes. Stereochemical selectivity is also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10241 / 10246
页数:6
相关论文
共 50 条
  • [1] Regio- and Stereoselective Copper(II)-Catalyzed Hydrosilylation of Activated Allenes in Water: Access to Vinylsilanes
    Pashikanti, Srinath
    Calderone, Joseph A.
    Nguyen, Matthew K.
    Sibley, Christopher D.
    Santos, Webster L.
    ORGANIC LETTERS, 2016, 18 (10) : 2443 - 2446
  • [2] Rhodium-catalyzed intramolecular hydrosilylation of allenes
    Commandeur, C
    Varchi, G
    Shimizu, K
    Ojima, I
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3248 - U3249
  • [3] Synthesis of Linear Allylsilanes via Molybdenum-Catalyzed Regioselective Hydrosilylation of Allenes
    Asako, Sobi
    Ishikawa, Sae
    Takai, Kazuhiko
    ACS CATALYSIS, 2016, 6 (05): : 3387 - 3395
  • [4] A new asymmetric synthesis of optically active allenes via metal catalyzed hydrosilylation
    Tillack, A
    Koy, C
    Michalik, D
    Fischer, C
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (01) : 116 - 121
  • [5] Regiodivergent and Stereoselective Hydrosilylation of 1,3-Disubstituted Allenes
    Miller, Zachary D.
    Dorel, Ruth
    Montgomery, John
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (31) : 9088 - 9091
  • [6] Ligandless Regioselective Hydrosilylation of Allenes Catalyzed by Gold Nanoparticles
    Kidonakis, Marios
    Stratakis, Manolis
    ORGANIC LETTERS, 2015, 17 (18) : 4538 - 4541
  • [7] A DFT Study on Palladium and Nickel-Catalyzed Regioselective and Stereoselective Hydrosilylation of 1,3-Disubstituted Allenes
    Xie, Hujun
    Kuang, Jian
    Wang, Lihong
    Li, Yang
    Huang, Lvtao
    Fan, Ting
    Lei, Qunfang
    Fang, Wenjun
    ORGANOMETALLICS, 2017, 36 (17) : 3371 - 3381
  • [8] Copper-Catalyzed Regiodivergent and Enantioselective Hydrosilylation of Allenes
    Xu, Jian-Lin
    Xu, Zhe-Yuan
    Wang, Zi-Lu
    Ma, Wei-Wei
    Sun, Xin-Yue
    Fu, Yao
    Xu, Yun-He
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (12) : 5535 - 5542
  • [10] Synthesis of α-tertiary allylsilanes by palladium-catalyzed hydrosilylation of 1,1-disubstituted allenes
    Li, Kaidi
    Nie, Ming
    Tang, Wenjun
    GREEN SYNTHESIS AND CATALYSIS, 2020, 1 (02): : 171 - 174