5-exo atom transfer cyclisation onto alkynes mediated by copper(I) complexes

被引:36
作者
Clark, AJ [1 ]
Battle, GM
Bridge, A
机构
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
[2] Aventis Pharma Ltd, Dagenham RM10 7XS, Essex, England
关键词
radicals and radical reactions; cyclisations; copper and compounds; alkynes;
D O I
10.1016/S0040-4039(01)00060-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Multidentate amine derived copper(I) halide complexes mediate the atom transfer radical cyclisation of 1-halo-N-propargylacetamides. While cyclisation of trichloro- and dichloroacetamide derivatives leads to alpha,beta -unsaturated gamma -lactams containing the gem-dihalide functional group, monohaloacetamides give rise to either cyclised atom transfer or reduction products depending upon the solvent and catalyst used. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1999 / 2001
页数:3
相关论文
共 21 条
  • [1] Synthesis of heterocycles by radical cyclisation
    Bowman, WR
    Bridge, CF
    Brookes, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (01): : 1 - 14
  • [2] FREE-RADICAL CYCLIZATIONS IN ALKALOID SYNTHESIS - (+)-HELIOTRIDINE AND (+)-HASTANECINE
    CHOI, JK
    HART, DJ
    [J]. TETRAHEDRON, 1985, 41 (19) : 3959 - 3971
  • [3] Ligand geometry effects in copper mediated atom transfer radical cyclisations.
    Clark, AJ
    Filik, RP
    Thomas, GH
    [J]. TETRAHEDRON LETTERS, 1999, 40 (26) : 4885 - 4888
  • [4] Efficient room temperature copper(I) mediated 5-endo radical cyclisations
    Clark, AJ
    Dell, CP
    Ellard, JM
    Hunt, NA
    McDonagh, JP
    [J]. TETRAHEDRON LETTERS, 1999, 40 (49) : 8619 - 8623
  • [5] N-alkyl-2-pyridylmethanimines as tuneable alternatives to bipyridine ligands in copper mediated atom transfer radical cyclisation.
    Clark, AJ
    Duncalf, DJ
    Filik, RP
    Haddleton, DM
    Thomas, GH
    Wongtap, H
    [J]. TETRAHEDRON LETTERS, 1999, 40 (19) : 3807 - 3810
  • [6] Solid-supported catalysts for atom-transfer radical cyclization of 2-haloacetamides
    Clark, AJ
    Filik, RP
    Haddleton, DM
    Radigue, A
    Sanders, CJ
    Thomas, GH
    Smith, ME
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) : 8954 - 8957
  • [7] ATOM TRANSFER ADDITION AND ANNULATION REACTIONS OF IODOMALONATES
    CURRAN, DP
    CHEN, MH
    SPLETZER, E
    SEONG, CM
    CHANG, CT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) : 8872 - 8878
  • [8] ATOM TRANSFER CYCLIZATION REACTIONS OF HEX-5-YNYL IODIDES - SYNTHETIC AND MECHANISTIC STUDIES
    CURRAN, DP
    CHEN, MH
    KIM, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) : 6265 - 6276
  • [9] ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES
    CURRAN, DP
    CHANG, CT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) : 3140 - 3157
  • [10] RECENT APPLICATIONS OF RADICAL REACTIONS IN NATURAL PRODUCT SYNTHESIS
    CURRAN, DP
    SISKO, J
    YESKE, PE
    LIU, H
    [J]. PURE AND APPLIED CHEMISTRY, 1993, 65 (06) : 1153 - 1159