Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes

被引:74
作者
Boden, CDJ [1 ]
Pattenden, G [1 ]
Ye, T [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 20期
关键词
D O I
10.1039/p19960002417
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical synthesis of (E)-1-stannylalk-1-enes containing a range of oxygen and nitrogen functionality is highlighted, involving hydrostannylation followed by palladium-catalysed carbon-bromine bond cleavage reactions of 1-bromoalkynes.
引用
收藏
页码:2417 / 2419
页数:3
相关论文
共 28 条
  • [1] Sequential sp(2)-sp(2) coupling reactions in polyene macrolide synthesis. A novel approach to macrolactin A
    Boyce, RJ
    Pattenden, G
    [J]. TETRAHEDRON LETTERS, 1996, 37 (20) : 3501 - 3504
  • [2] CAPELLA L, 1991, SYNTHESIS-STUTTGART, P1201
  • [3] USEFUL NEW ORGANOMETALLIC REAGENTS FOR SYNTHESIS OF ALLYLIC ALCOHOLS BY NUCLEOPHILIC VINYLATION
    COREY, EJ
    WOLLENBERG, RH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) : 2265 - 2266
  • [4] ELABORATION OF THE SIDE-CHAIN OF ALPHA-AMINO-ACIDS BY PALLADIUM-CATALYZED STILLE COUPLINGS
    CRISP, GT
    GLINK, PT
    [J]. TETRAHEDRON, 1994, 50 (10) : 3213 - 3234
  • [5] Total synthesis of the virginiamycin antibiotic 14,15-anhydropristinamycin IIB
    Entwistle, DA
    Jordan, SI
    Montgomery, J
    Pattenden, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12): : 1315 - 1317
  • [6] AN IMPROVED PROCEDURE FOR ALDEHYDE-TO-ALKYNE HOMOLOGATION VIA 1,1-DIBROMOALKENES - SYNTHESIS OF 1-BROMOALKYNES
    GRANDJEAN, D
    PALE, P
    CHUCHE, J
    [J]. TETRAHEDRON LETTERS, 1994, 35 (21) : 3529 - 3530
  • [7] GREEVES N, 1994, SYNLETT, P537
  • [8] REGIOSELECTIVE STANNLYMETALLATION OF ACETYLENES IN THE PRESENCE OF TRANSITION-METAL CATALYST
    HIBINO, J
    MATSUBARA, S
    MORIZAWA, Y
    OSHIMA, K
    NOZAKI, H
    [J]. TETRAHEDRON LETTERS, 1984, 25 (20) : 2151 - 2154
  • [9] SCOPE OF THE CHROMIUM(II)-MEDIATED SYNTHESIS OF E-ALKENYLSTANNANES FROM ALDEHYDES AND BU(3)SNCHBR(2)
    HODGSON, DM
    BOULTON, LT
    MAW, GN
    [J]. TETRAHEDRON, 1995, 51 (12) : 3713 - 3724
  • [10] A NOVEL ENTRY TO 17-ALPHA-BROMOETHYNYL AND 17-ALPHA-IODOETHYNYL STEROIDS
    HOFMEISTER, H
    ANNEN, K
    LAURENT, H
    WIECHERT, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (09): : 727 - 729