3-Component palladium-indium mediated diastereoselective cascade allylation of imines with allenes and aryl iodides

被引:72
作者
Cooper, IR [1 ]
Grigg, R
MacLachlan, WS
Thornton-Pett, M
Sridharan, V
机构
[1] Univ Leeds, Sch Chem, Mol Innovat Divers & Automated Synth Ctr, Leeds LS2 9JT, W Yorkshire, England
[2] GlaxoSmithkline, Harlow CM19 5AW, Essex, England
关键词
D O I
10.1039/b202940e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new palladium-indium diastereoselective cascade allylation of imines using allenes and aryl iodides is described; N-tosyl and N-aryl homoallyl amines were obtained in moderate to good yields and excellent diastereoselectivity was observed when enantiomerically pure N-tert-butane-sulfinyl imines were employed in the cascade.
引用
收藏
页码:1372 / 1373
页数:2
相关论文
共 14 条
  • [1] The use of enantiomerically pure N-sulfinimines in asymmetric Baylis-Hillman reactions
    Aggarwal, VK
    Castro, AMM
    Mereu, A
    Adams, H
    [J]. TETRAHEDRON LETTERS, 2002, 43 (08) : 1577 - 1581
  • [2] Palladium-indium mediated Barbier-type allylation of aldehydes with allenes
    Anwar, U
    Grigg, R
    Rasparini, M
    Savic, V
    Sridharan, V
    [J]. CHEMICAL COMMUNICATIONS, 2000, (08) : 645 - 646
  • [3] Palladium catalysed cyclisation-Barbier-type allylation cascades
    Anwar, U
    Grigg, R
    Sridharan, V
    [J]. CHEMICAL COMMUNICATIONS, 2000, (11) : 933 - 934
  • [4] A new preparative method for allylic indium(III) reagents by reductive transmetalation of π-allylpalladium(II) with indium(I) salts
    Araki, S
    Kamei, T
    Hirashita, T
    Yamamura, H
    Kawai, M
    [J]. ORGANIC LETTERS, 2000, 2 (06) : 847 - 849
  • [5] *CCDC, 181904 CCDC
  • [6] A new cascade for the one-pot synthesis of linear homoallylic alcohols with an allylic diindium reagent
    Hirashita, T
    Yamamura, H
    Kawai, M
    Araki, S
    [J]. CHEMICAL COMMUNICATIONS, 2001, (04) : 387 - 388
  • [7] Kumar HMS, 2000, TETRAHEDRON LETT, V41, P9311
  • [8] Organic syntheses using indium-mediated and catalyzed reactions in aqueous media
    Li, CJ
    Chan, TH
    [J]. TETRAHEDRON, 1999, 55 (37) : 11149 - 11176
  • [9] Indium-mediated organometallic reactions in aqueous media. Stereoselectivity in the crotylation of sulfonimines bearing a proximal chelating group
    Lu, WS
    Chan, TH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) : 3467 - 3473
  • [10] Lui G., 1999, J ORG CHEM, V64, P1278