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
  • [21] Anomalous products from intramolecular C-H insertion by a rhodium carbenoid. Possible involvement of a zwitterionic mechanism
    White, JD
    Hrnciar, P
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19): : 7271 - 7273
  • [22] Rh(II)-catalyzed enantioselective synthesis of acuminatin through a C-H insertion reaction of a non-stabilized carbenoid
    Lopez-Sanchez, Cristobal
    Alvarez-Corral, Miriam
    Jimenez-Gonzalez, Leticia
    Munoz-Dorado, Manuel
    Rodriguez-Garcia, Ignacio
    TETRAHEDRON, 2013, 69 (26) : 5511 - 5516
  • [23] Asymmetric synthesis of secondary alcohols from primary alcohols via intramolecular carbenoid C-H insertion catalyzed by rhodium(II) 3-phenylcholestane-2-carboxylate
    Hwang, CH
    Chong, YH
    Song, SY
    Kwak, HS
    Lee, E
    CHEMICAL COMMUNICATIONS, 2004, (07) : 816 - 817
  • [24] Reactivity and selectivity of ortho-metalated Rhodium(II) complexes in C-H insertion reactions of α-diazo compounds
    Estevan, F
    Lahuerta, P
    Perez-Prieto, J
    Pereira, I
    Stiriba, SE
    ORGANOMETALLICS, 1998, 17 (16) : 3442 - 3447
  • [25] RHODIUM CARBENOID MEDIATED CYCLIZATIONS - INTRAMOLECULAR CYCLOPROPANATION AND C-H INSERTION REACTIONS DERIVED FROM TYPE-II O-ALKYNYL SUBSTITUTED ALPHA-DIAZOACETOPHENONES
    MUELLER, PH
    KASSIR, JM
    SEMONES, MA
    WEINGARTEN, MD
    PADWA, A
    TETRAHEDRON LETTERS, 1993, 34 (27) : 4285 - 4288
  • [26] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion
    Davies, HML
    Beckwith, REJ
    CHEMICAL REVIEWS, 2003, 103 (08) : 2861 - 2903
  • [27] CARBENE C-H INSERTION REACTIONS
    HASZELDINE, RN
    SPEIGHT, JG
    CHEMICAL COMMUNICATIONS, 1967, (19) : 995 - +
  • [28] Solid-phase rhodium carbenoid N-H insertion reactions: the synthesis of a diverse array of indoles
    Lee, SH
    Clapham, B
    Koch, G
    Zimmermann, J
    Janda, KD
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (02): : 188 - 196
  • [29] Synthesis of natural products by rhodium-mediated intramolecular C-H insertion
    Taber, DF
    Stiriba, SE
    CHEMISTRY-A EUROPEAN JOURNAL, 1998, 4 (06) : 990 - 992
  • [30] Rhodium(III)-catalyzed sulfonamide directed ortho C-H carbenoid functionalization via metal carbene migratory insertion
    Dong, Yi
    Chen, Jiajing
    Xu, Heng
    CHEMICAL COMMUNICATIONS, 2019, 55 (14) : 2027 - 2030