Cu(I)-NHC Catalyzed Asymmetric Silyl Transfer to Unsaturated Lactams and Amides

被引：83
作者：
Pace, Vittorio [1 ]
Rae, James P. [1 ]
Procter, David J. [1 ]
机构：
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 02期
基金：
英国工程与自然科学研究理事会;
关键词：
SI-B BOND; CONJUGATE ADDITION; ORGANIC-SYNTHESIS; PHENYLDIMETHYLSILYL GROUP; ALPHA; BETA-UNSATURATED ACCEPTORS; ENANTIOSELECTIVE SYNTHESIS; SILAFUNCTIONAL COMPOUNDS; SAMARIUM(II) IODIDE; CARBON BOND; SILICON;
D O I：
10.1021/ol4033623
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first asymmetric silylation of unsaturated lactams and amides using Cu(I)-NHC catalysts and PhMe(2)SiBpin has been accomplished. The method has been exploited in an expedient asymmetric synthesis of the (R)-enantiomer of the nootropic drug oxiracetam.
引用
收藏
页码：476 / 479
页数：4
相关论文
共 67 条
  • [61] SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .20. HYDROGEN-PEROXIDE OXIDATION OF THE SILICON-CARBON BOND IN ORGANOALKOXYSILANES
    TAMAO, K
    ISHIDA, N
    TANAKA, T
    KUMADA, M
    [J]. ORGANOMETALLICS, 1983, 2 (11) : 1694 - 1696
  • [62] Catalytic asymmetric C-Si bond formation to acyclic α,β-unsaturated acceptors by RhI-catalyzed conjugate silyl transfer using a Si-B linkage
    Walter, Christian
    Oestreich, Martin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) : 3818 - 3820
  • [63] Rhodium-catalyzed enantioselective conjugate silyl transfer: 1,4-addition of silyl boronic esters to cyclic enones and lactones
    Walter, Christian
    Auer, Gertrud
    Oestreich, Martin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (34) : 5675 - 5677
  • [64] Rhodium(I)-catalyzed enantioselective 1,4-addition of nucleophilic silicon
    Walter, Christian
    Froehlich, Roland
    Oestreich, Martin
    [J]. TETRAHEDRON, 2009, 65 (28) : 5513 - 5520
  • [65] Copper-Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons
    Welle, Alexandre
    Petrignet, Julien
    Tinant, Bernard
    Wouters, Johan
    Riant, Olivier
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (36) : 10980 - 10983
  • [66] The recent synthesis and application of silicon-stereogenic silanes: A renewed and significant challenge in asymmetric synthesis
    Xu, Li-Wen
    Li, Li
    Lai, Guo-Qiao
    Jiang, Jian-Xiong
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) : 1777 - 1790
  • [67] Cu(II)-Catalyzed Allylic Silylation of Morita-Baylis-Hillman Alcohols via Dual Activation of Si-B Bond and Hydroxyl Group
    Xuan, Qing-Qing
    Zhong, Neng-Jun
    Ren, Chuan-Li
    Liu, Li
    Wang, Dong
    Chen, Yong-Jun
    Li, Chao-Jun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) : 11076 - 11081
1234567