Catalytic Enantioselective Synthesis of Alkenylhydrosilanes

被引:110
|
作者
Igawa, Kazunobu [1 ]
Yoshihiro, Daisuke [2 ]
Ichikawa, Nobumasa [2 ]
Kokan, Naoto [3 ]
Tomooka, Katsuhiko [1 ]
机构
[1] Kyushu Univ, Inst Mat Chem & Engn, Fukuoka 8168580, Japan
[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Fukuoka 8168580, Japan
[3] Tokyo Inst Technol, Dept Appl Chem, Tokyo, Japan
关键词
asymmetric synthesis; enantioselectivity; hydrosilylation; ozone; silanes; ASYMMETRIC-SYNTHESIS; RACEMIC ACETYL(TERT-BUTYL)METHYLPHENYLSILANE; EFFICIENT APPROACH; SILICON; DERIVATIVES; HYDROSILYLATION; SILANES; COMPLEXES; KETONES; ALKYNES;
D O I
10.1002/anie.201207361
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric silanes: A synthesis of nonracemic alkenylhydrosilanes has been developed based on the desymmetrization of a dihydrosilane through alkenylation with an alkyne using an asymmetric catalyst. The alkenylhydrosilane product can be used as a versatile chiral building block for other functionalized nonracemic silanes through the stereoselective conversion of its hydride and/or alkenyl moiety. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12745 / 12748
页数:4
相关论文
共 50 条
  • [41] Enantioselective synthesis of indoles through catalytic indolization
    Yang, Bin-Miao
    Ng, Xiao Qian
    Zhao, Yu
    CHEM CATALYSIS, 2022, 2 (11): : 3048 - 3076
  • [42] Catalytic enantioselective Michael addition in the synthesis of α-aminophosphonates
    Jászay, ZM
    Németh, G
    Pham, TS
    Petneházy, I
    Grün, A
    Toke, L
    TETRAHEDRON-ASYMMETRY, 2005, 16 (23) : 3837 - 3840
  • [43] Synthesis of (+)-ribostamycin by catalytic, enantioselective hydroamination of benzene
    Ungarean, Chad N.
    Galer, Petra
    Zhang, Yu
    Lee, Ken S.
    Ngai, Justin M.
    Lee, Sungjong
    Liu, Peng
    Sarlah, David
    NATURE SYNTHESIS, 2022, 1 (07): : 542 - 547
  • [44] Catalytic enantioselective total synthesis of (+)-eucomic acid
    Estipona, Benzi I.
    Pritchett, Beau P.
    Craig, Robert A., II
    Stoltz, Brian M.
    TETRAHEDRON, 2016, 72 (26) : 3707 - 3712
  • [45] Highly enantioselective catalytic synthesis of chiral pyridines
    Ravindra P. Jumde
    Francesco Lanza
    Tilde Pellegrini
    Syuzanna R. Harutyunyan
    Nature Communications, 8
  • [46] Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C
    Jessen, Henning J.
    Schumacher, Andreas
    Schmid, Fabian
    Pfaltz, Andreas
    Gademann, Karl
    ORGANIC LETTERS, 2011, 13 (16) : 4368 - 4370
  • [47] Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids
    Yang, Zhenyu
    He, Ying
    Toste, F. Dean
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (31) : 9775 - 9778
  • [48] Catalytic enantioselective synthesis of axially chiral allenes
    Ogasawara, Masamichi
    TETRAHEDRON-ASYMMETRY, 2009, 20 (03) : 259 - 271
  • [49] Catalytic Enantioselective Synthesis of Planar Chiral Cyclophanes
    Tanaka, Ken
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2018, 91 (02) : 187 - 194
  • [50] Synthesis of (+)-ribostamycin by catalytic, enantioselective hydroamination of benzene
    Chad N. Ungarean
    Petra Galer
    Yu Zhang
    Ken S. Lee
    Justin M. Ngai
    Sungjong Lee
    Peng Liu
    David Sarlah
    Nature Synthesis, 2022, 1 : 542 - 547