Rhodium(II) catalysed three-component coupling: a novel reaction of in situ generated iodonium ylides

被引:9
作者
Bonge, Hanne Therese [1 ]
Hansen, Tore [1 ]
机构
[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway
关键词
D O I
10.1016/j.tetlet.2007.11.021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclic ethers are cleaved in the presence of nitromethane, a base, a hypervalent iodine compound and a Rh(II) catalyst to give nitromethoxy acetates in up to 71% isolated yields. The reaction is a three-component coupling of an ether with a nitromethane derived carbenoid and a carboxylate group originating from the hypervalent iodine compound. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:57 / 61
页数:5
相关论文
共 18 条
  • [1] Antkowiak WZ, 2001, POL J CHEM, V75, P875
  • [2] RhII-catalyzed cycloadditions of carbomethoxy iodonium ylides
    Batsila, C
    Kostakis, G
    Hadjiarapoglou, LP
    [J]. TETRAHEDRON LETTERS, 2002, 43 (34) : 5997 - 6000
  • [3] Cyclopropanation of alkenes using hypervalent iodine reagents
    Biland, AS
    Altermann, S
    Wirth, T
    [J]. ARKIVOC, 2003, : 164 - 169
  • [4] Cyclopropanation of olefins with nitromethane
    Bonge, Hanne Therese
    Hansen, Tore
    [J]. SYNLETT, 2007, (01) : 55 - 58
  • [5] CLARK JS, 2002, NITROGEN OXYGEN SULF, V13
  • [6] Copper-catalyzed nitrogen transfer mediated by iodosylbenzene PhI=O
    Dauban, P
    Sanière, L
    Tarrade, A
    Dodd, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) : 7707 - 7708
  • [7] Rhodium(II)-catalyzed inter- and intramolecular cyclopropanations with diazo compounds and phenyliodonium ylides: Synthesis and chiral analysis
    Ghanem, A
    Lacrampe, F
    Schurig, V
    [J]. HELVETICA CHIMICA ACTA, 2005, 88 (02) : 216 - 239
  • [8] One-pot synthesis and chiral analysis of cyclopropane derivatives
    Ghanem, A
    Aboul-Enein, HY
    Müller, P
    [J]. CHIRALITY, 2005, 17 (01) : 44 - 50
  • [9] Lin SJ, 1997, HETEROCYCLES, V45, P1879
  • [10] Expedient synthesis of cyclopropane α-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate
    Moreau, B
    Charette, AB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) : 18014 - 18015