Stereoselective synthesis of halocyclopropanes via halogenation of cyclopropylindium reagents

被引:25
作者
Araki, S [1 ]
Kenji, O [1 ]
Shiraki, F [1 ]
Hirashita, T [1 ]
机构
[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
cyclopropanes; cyclopropenes; halogenation; indium and compounds;
D O I
10.1016/S0040-4039(02)01963-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stercoselective synthesis of halocyclopropanes has been achieved via halogenation of the cyclopropylindium reagents prepared from allylindation of cyclopropenes. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8033 / 8035
页数:3
相关论文
共 17 条
  • [1] Araki S, 2001, CHEM-EUR J, V7, P2784, DOI 10.1002/1521-3765(20010702)7:13<2784::AID-CHEM2784>3.0.CO
  • [2] 2-A
  • [3] APPLICATION OF INDIUM ATE COMPLEXES TO SYNTHETIC CHEMISTRY - SELECTIVE CONJUGATE ADDITION TO ENONES AND COUPLING WITH ALLYLIC HALIDES
    ARAKI, S
    SHIMIZU, T
    JIN, SJ
    BUTSUGAN, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (12) : 824 - 825
  • [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] Stereodivergent allylindation of cyclopropenes. Remarkable stereodirection and acceleration by neighbouring carboxyl and hydroxyl groups
    Araki, S
    Nakano, H
    Subburaj, K
    Hirashita, T
    Shibutani, K
    Yamamura, H
    Kawai, M
    Butsugan, Y
    [J]. TETRAHEDRON LETTERS, 1998, 39 (35) : 6327 - 6330
  • [6] Chelation-controlled regio- and stereoselective allylindation of norbornenols
    Araki, S
    Kamei, T
    Igarashi, Y
    Hirashita, T
    Yamamura, H
    Kawai, M
    [J]. TETRAHEDRON LETTERS, 1999, 40 (45) : 7999 - 8002
  • [7] CYCLIC STEREOCONTROL VIA ORGANOBISMETALLIC REAGENTS .6. STEREODEFINED SUBSTITUTED CYCLOPROPYL ZINC REAGENTS
    BERUBEN, D
    MAREK, I
    NORMANT, JF
    PLATZER, N
    [J]. TETRAHEDRON LETTERS, 1993, 34 (47) : 7575 - 7578
  • [8] Allyl- and benzylindium reagents. Carboindation of carbon-carbon and carbon-nitrogen triple bonds
    Fujiwara, N
    Yamamoto, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) : 4095 - 4101
  • [9] Allylation of unactivated and/or functionalized alkynes with allylindiums
    Fujiwara, N
    Yamamoto, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) : 2318 - 2319
  • [10] SYNTHESIS OF HOMOALLYLAMINES BY THE ADDITION OF ALLYLIC INDIUM REAGENTS TO AZOMETHINES AND NITRILES
    JIN, SJ
    ARAKI, S
    BUTSUGAN, Y
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (05) : 1528 - 1532