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
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
  • [32] Application of Parallel Synthesis Techniques to asymmetric rhodium(II) carbenoid insertion into the Si-H bond.
    Buck, RT
    Moody, CJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U407 - U407
  • [33] Isoquinolone synthesis via rhodium (II) catalyzed intramolecular aromatic C-H insertion of α-phenylsulfonyl-α-diazoacetamides
    Jung, KW
    Nagle, AS
    Yoon, CH
    Chen, CL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U398 - U398
  • [34] Rhodium(II)-catalysed intramolecular C-H insertion α- to oxygen: reactivity, selectivity and applications to natural product synthesis
    Lombard, Fanny J.
    Coster, Mark J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (23) : 6419 - 6431
  • [35] Recent progress in asymmetric intermolecular C-H activation by rhodium carbenoid intermediates
    Davies, HML
    Antoulinakis, EG
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) : 47 - 55
  • [36] Stereochemical Outcome of Copper-Catalyzed C-H Insertion Reactions. An Experimental and Theoretical Study
    Jimenez-Oses, Gonzalo
    Vispe, Eugenio
    Roldan, Marta
    Rodriguez-Rodriguez, Sergio
    Lopez-Ram-de-Viu, Pilar
    Salvatella, Luis
    Mayoral, Jose A.
    Fraile, Jose M.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12): : 5851 - 5857
  • [37] Theoretical Investigation of Chemoselectivity between C-H Insertion and Amide Insertion in Intramolecular Rhodium-Carbene Reactions
    Furuya, Tsukasa
    Ikeda, Kotaro
    Harada, Shingo
    Nemoto, Tetsuhiro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2023, 71 (02) : 107 - 110
  • [38] Rhodium carbenoid N-H insertion reactions of primary ureas: Solution and solid-phase synthesis of imidazolones
    Lee, SH
    Clapham, B
    Koch, G
    Zimmermann, J
    Janda, KD
    ORGANIC LETTERS, 2003, 5 (04) : 511 - 514
  • [39] Late-stage C-H functionalization of complex alkaloids and drug molecules via intermolecular rhodium-carbenoid insertion
    He, Jing
    Hamann, Lawrence G.
    Davies, Huw M. L.
    Beckwith, Rohan E. J.
    NATURE COMMUNICATIONS, 2015, 6
  • [40] anti -Selective Synthesis of Substituted β-Homoprolines by Rhodium Alkyl Nitrene C-H Insertion
    Tang, Xinxin
    Noda, Hidetoshi
    Shibasaki, Masakatsu
    SYNLETT, 2024, 35 (10) : 1131 - 1134