Copper-Catalyzed Highly Enantioselective Carbenoid Insertion into Si-H Bonds

被引：118
作者：
Zhang, Yong-Zhen
Zhu, Shou-Fei
Wang, Li-Xin
Zhou, Qi-Lin [1 ]
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 44期
关键词：
asymmetric catalysis; carbenoids; copper; insertion; N ligands;
D O I：
10.1002/anie.200803192
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Complete control: A highly efficient, copper-catalyzed, asymmetric carbenoid insertion into Si-H bonds, using chiral spiro diimine (SIDIM) ligands (see scheme, Ar=2,6-Cl2C 6H3, OTf=trifluoromethanesulfonate), produces a wide range of α-silylesters, in high yields with excellent enantiomeric excesses. This catalytic system offers unprecedented levels of enantiocontrol for the Si-H bond insertion reaction. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：8496 / 8498
页数：3
相关论文
共 25 条
  • [1] SYNTHESIS OF ALPHA-(ALKOXYSILYL)ACETIC ESTERS - A ROUTE TO 1,2-DIOLS
    ANDREY, O
    LANDAIS, Y
    PLANCHENAULT, D
    WEBER, V
    [J]. TETRAHEDRON, 1995, 51 (44) : 12083 - 12096
  • [2] ANDREY O, 1993, TETRAHEDRON LETT, V34, P2977
  • [3] A NEW AND GENERAL-SYNTHESIS OF ALPHA-SILYL CARBONYL-COMPOUNDS BY SI-H INSERTION FROM TRANSITION-METAL CATALYZED-REACTIONS OF DIAZO ESTERS AND DIAZO KETONES
    BAGHERI, V
    DOYLE, MP
    TAUNTON, J
    CLAXTON, EE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) : 6158 - 6160
  • [4] BAIKOV VE, 1981, J GEN CHEM USSR, V51, P1858
  • [5] Asymmetric rhodium carbene insertion into the Si-H bond: identification of new dirhodium(II) carboxylate catalysts using parallel synthesis techniques
    Buck, RT
    Coe, DM
    Drysdale, MJ
    Ferris, L
    Haigh, D
    Moody, CJ
    Pearson, ND
    Sanghera, JB
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (07) : 791 - 816
  • [6] Asymmetric rhodium carbenoid insertion into the Si-H bond
    Buck, RT
    Doyle, MP
    Drysdale, MJ
    Ferris, L
    Forbes, DC
    Haigh, D
    Moody, CJ
    Pearson, ND
    Zhou, QL
    [J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7631 - 7634
  • [7] Parallel synthesis techniques in the identification of new chiral dirhodium(II) carboxylates for asymmetric carbenoid insertion reactions
    Buck, RT
    Coe, DM
    Drysdale, MJ
    Moody, CJ
    Pearson, ND
    [J]. TETRAHEDRON LETTERS, 1998, 39 (39) : 7181 - 7184
  • [8] A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds
    Bulugahapitiya, P
    Landais, Y
    ParraRapado, L
    Planchenault, D
    Weber, V
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) : 1630 - 1641
  • [9] Highly enantioselective insertion of carbenoids into o-h bonds of phenols:: An efficient approach to chiral α-aryloxycarboxylic esters
    Chen, Chao
    Zhu, Shou-Fei
    Liu, Bin
    Wang, Li-Xin
    Zhou, Qi-Lin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) : 12616 - +
  • [10] Preparation and application of chiral spiro nitrogen-containing ligands for cobalt-catalyzed asymmetric Michael addition
    Chen, Chao
    Zhu, Shou-Fei
    Wu, Xin-Yan
    Zhou, Qi-Lin
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (19) : 2761 - 2767
123