Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents

被引:64
|
作者
Endo, Kohei [1 ]
Ogawa, Mika [1 ]
Shibata, Takanori [1 ]
机构
[1] Waseda Univ, Dept Chem & Biochem, Sch Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan
关键词
alkylation; synthetic methods; copper; Michael addition; zinc; MANNICH-TYPE REACTION; BETA-AMINO ALCOHOLS; GRIGNARD-REAGENTS; ET2ZN/LINKED-BINOL COMPLEX; ACYCLIC ENONES; ENANTIOSELECTIVE HYDROGENATION; QUATERNARY CENTERS; MICHAEL REACTION; ALDOL REACTION; LINKED-BINOL;
D O I
10.1002/anie.200906839
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) A whole lot o' metal: An efficient copper-catalyzed asymmetric conjugate addition was achieved using a binol-derived ligand. The catalytic system has a turnover number of 2000, and the excellent cata-lytic performance could be attributed to the generation of a multinuclear complex such as 1. binol = 2, 2'-dihydroxy-l, 1'-binaphthyl. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2410 / 2413
页数:4
相关论文
共 50 条
  • [1] Aminohydroxyphosphine ligand for the copper-catalyzed enantioselective conjugate addition of organozinc reagents
    Hajra, Alakananda
    Yoshikai, Naohiko
    Nakamura, Eiichi
    ORGANIC LETTERS, 2006, 8 (18) : 4153 - 4155
  • [2] Recent Advances in Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents
    Tang, Fengxiang
    Ye, Jiuyong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (07) : 1414 - 1427
  • [3] Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones
    Feringa, BL
    Badorrey, R
    Peña, D
    Harutyunyan, SR
    Minnaard, AJ
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) : 5834 - 5838
  • [4] Copper-catalyzed asymmetric conjugate addition with Grignard reagents and SimplePhos ligands
    Palais, Laetitia
    Alexakis, Alexandre
    TETRAHEDRON-ASYMMETRY, 2009, 20 (24) : 2866 - 2870
  • [5] Formation of Quaternary Centers by Copper-Catalyzed Asymmetric Conjugate Addition of Alkylzirconium Reagents
    Sidera, Mireia
    Roth, Philippe M. C.
    Maksymowicz, Rebecca M.
    Fletcher, Stephen P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) : 7995 - 7999
  • [6] Chiral NHC Ligands for the Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents
    Germain, Nicolas
    Magrez, Magaly
    Kehrli, Stefan
    Mauduit, Marc
    Alexakis, Alexandre
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (27) : 5301 - 5306
  • [7] Unprecedented copper-catalyzed asymmetric conjugate addition of organometallic reagents to α,β-unsaturated lactams
    Pineschi, M
    Del Moro, F
    Gini, F
    Minnaard, AJ
    Feringa, BL
    CHEMICAL COMMUNICATIONS, 2004, (10) : 1244 - 1245
  • [8] Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors
    Schmid, Thibault E.
    Drissi-Amraoui, Sammy
    Crevisy, Christophe
    Basle, Olivier
    Mauduit, Marc
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 2418 - 2434
  • [9] BINAM-mono-PHOS as New Entry for Multinuclear Copper Catalysts in Asymmetric Conjugate Addition of Organozinc Reagents
    Endo, Kohei
    Takayama, Ryotaro
    Shibata, Takanori
    SYNLETT, 2013, 24 (09) : 1155 - 1159
  • [10] Copper-catalyzed asymmetric allylic substitution reactions with organozinc and Grignard reagents
    Geurts, Koen
    Fletcher, Stephen P.
    van Zijl, Anthoni W.
    Minnaard, Adriaan J.
    Feringa, Ben L.
    PURE AND APPLIED CHEMISTRY, 2008, 80 (05) : 1025 - 1037