Synthesis of spirosystems by rhodium(II)-carbenoid C-H insertion reactions.

被引：14
|
作者：
Aburel, PS [1 ]
Undheim, K [1 ]
机构：
[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 22期
关键词：
D O I：
10.1016/S0040-4039(98)00591-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple one-pot procedure is described for the preparation of spiro[4,4]nonane-2,7-dione derivatives from open chain bis(alpha-diazoketones). The reactions proceed by an intramolecular Rh(II)-carbenoid insertion into a methylene C-H bond yielding a cyclopentane which subsequently undergoes C-H methine insertion and cyclopentyl spiroannulation. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3813 / 3814
页数：2
相关论文
共 50 条
  • [1] Rhodium(II)-carbenoid C-H insertion reactions in the synthesis of α,β′-dioxospirane systems
    Aburel, PS
    Romming, C
    Undheim, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, Royal Society of Chemistry (09): : 1024 - 1029
  • [2] Rhodium(II)-carbenoid C-H insertion reactions in the synthesis of β-oxospirane systems
    Aburel, PS
    Undheim, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12): : 1891 - 1896
  • [3] An enantiospecific synthesis of (-)-2-pupukeanone via a rhodium carbenoid C-H insertion reaction
    Srikrishna, A
    Kumar, PR
    Gharpure, SJ
    TETRAHEDRON LETTERS, 2001, 42 (23) : 3929 - 3931
  • [4] MODEL STUDIES OF THE STEREOELECTRONIC EFFECT IN RH(II) MEDIATED CARBENOID C-H INSERTION REACTIONS
    WANG, P
    ADAMS, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) : 3296 - 3305
  • [5] REGIOSELECTIVE RH (II) MEDIATED CARBENOID C-H INSERTION REACTIONS DICTATED BY ELECTRONIC INDUCTION
    WANG, P
    ADAMS, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 70 - MEDI
  • [6] RHODIUM(II) TRIFLUOROACETAMIDE - AN EXCELLENT CATALYST FOR CARBENOID O-H INSERTION REACTIONS
    COX, GG
    KULAGOWSKI, JJ
    MOODY, CJ
    SIE, ERHB
    SYNLETT, 1992, (12) : 975 - 976
  • [7] New highly fluorinated dirhodium(II) tetrakis(alkanecarboxylates) as catalysts for carbenoid C-H insertion reactions
    Endres, A
    Maas, G
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 643 : 174 - 180
  • [8] Synthesis of Benzodihydrofurans by Asymmetric C-H Insertion Reactions of Donor/Donor Rhodium Carbenes
    Lamb, Kellan N.
    Squitieri, Richard A.
    Chintala, Srinivasa R.
    Kwong, Ada J.
    Balmond, Edward I.
    Soldi, Cristian
    Dmitrenko, Olga
    Reis, Marta Castineira
    Chung, Ryan
    Addison, J. Bennett
    Fettinger, James C.
    Hein, Jason E.
    Tantillo, Dean J.
    Fox, Joseph M.
    Shaw, Jared T.
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (49) : 11843 - 11855
  • [9] Asymmetric Total Synthesis of (-)-trans-Blechnic Acid via Rhodium(II)-Catalyzed C-H Insertion and Palladium(II)-Catalyzed C-H Olefination Reactions
    Ito, Motoki
    Namie, Ryosuke
    Krishnamurthi, Janagiraman
    Miyamae, Hitomi
    Takeda, Koji
    Nambu, Hisanori
    Hashimoto, Shunichi
    SYNLETT, 2014, 25 (02) : 288 - 292
  • [10] Stereo- and regiocontrol in the formation of lactams by rhodium-carbenoid C-H insertion of α-diazoacetamides
    Gois, PMP
    Afonso, CAM
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (18) : 3773 - 3788
12345