Diastereoselective Carbometalation of Oxa- and Azabicyclic Alkenes under Iron Catalysis

被引:70
作者
Ito, Shingo [1 ,2 ]
Itoh, Takuma [1 ,2 ]
Nakamura, Masaharu [1 ,2 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Inst Chem Res, Int Res Ctr Elements Sci, Kyoto 6110011, Japan
[2] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Kyoto 6110011, Japan
关键词
bicyclic alkenes; carbometalation; diastereoselectivity; diphosphine ligands; iron; RING-OPENING REACTIONS; SECONDARY ALKYL-HALIDES; OXABICYCLIC ALKENES; GRIGNARD-REAGENTS; ENANTIOSELECTIVE DESYMMETRIZATION; ASYMMETRIC CYCLODIMERIZATION; UNSATURATED DICARBOXIMIDES; HYDROARYLATION; ALKENYLATION; LIGAND;
D O I
10.1002/anie.201006180
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly diastereoselective carbometalation of oxa- and azabicyclic alkenes with arylzinc reagents has been achieved by using FeCl3 and novel ortho-phenylene diphosphine ligands (see scheme; E=electrophile). The carbozincation products are stable towards β-heteroatom elimination and can be trapped with various electrophiles. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:454 / 457
页数:4
相关论文
共 81 条
  • [1] Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: Scope and limitations
    Allen, Anna
    Le Marquand, Paul
    Burton, Ryan
    Villeneuve, Karine
    Tam, William
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) : 7849 - 7857
  • [2] [Anonymous], 2009, ANGEW CHEM
  • [3] Aryl Norbornanes and Analogues via Palladium-Catalyzed Hydroarylation with Arenediazonium Tetrafluoroborates
    Bartoli, Gabriele
    Cacchi, Sandro
    Fabrizi, Giancarlo
    Goggiamani, Antonella
    [J]. SYNLETT, 2008, (16) : 2508 - 2512
  • [4] Recent Advances in Iron Catalysis in Organic Synthesis
    Bauer, Eike B.
    [J]. CURRENT ORGANIC CHEMISTRY, 2008, 12 (16) : 1341 - 1369
  • [5] Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens
    Bedford, RB
    Bruce, DW
    Frost, RM
    Hird, M
    [J]. CHEMICAL COMMUNICATIONS, 2005, (33) : 4161 - 4163
  • [6] Iron-catalyzed reactions in organic synthesis
    Bolm, C
    Legros, J
    Le Paih, J
    Zani, L
    [J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254
  • [7] Stereoselective Transformations of meso Bicyclic Hydrazines: Versatile Access to Functionalized Aminocyclopentanes
    Bournaud, Chloee
    Chung, Florence
    Luna, Alejandro Perez
    Pasco, Morgane
    Errasti, Gauthier
    Lecourt, Thomas
    Micouin, Laurent
    [J]. SYNTHESIS-STUTTGART, 2009, (06): : 869 - 887
  • [8] On the Role of Metal Contaminants in Catalyses with FeCl3
    Buchwald, Stephen L.
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) : 5586 - 5587
  • [9] Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents
    Cabrera, S
    Arrayás, RG
    Alonso, I
    Carretero, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) : 17938 - 17947
  • [10] Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199