Simple and efficient heterogeneous copper catalysts for enantioselective C-H carbene insertion

被引:87
作者
Fraile, Jose M. [1 ]
Garcia, Jose I.
Mayoral, Jose A.
Roldan, Marta
机构
[1] Univ Zaragoza, Dept Quim Organ, Inst Ciencia Mat Aragon, E-50009 Zaragoza, Spain
[2] Univ Zaragoza, CSIC, Inst Univ Catalisis Homogenea, E-50009 Zaragoza, Spain
关键词
D O I
10.1021/ol070092y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Immobilized box-Cu complexes are able to efficiently catalyze the insertion of a carbene, from methyl phenyldiazoacetate, into C-H bonds of THF, with high enantioselectivity (up to 88% ee). The immobilization not only allows recovery and reuse of the enantioselective catalyst but also provides an improvement in the selectivities from the values obtained in solution, probably due to a confinement effect of the bidimensional support.
引用
收藏
页码:731 / 733
页数:3
相关论文
共 32 条
  • [11] C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis
    Desimoni, Giovanni
    Faita, Giuseppe
    Jorgensen, Karl Anker
    [J]. CHEMICAL REVIEWS, 2006, 106 (09) : 3561 - 3651
  • [12] Copper, silver and gold-based catalysts for carbene addition or insertion reactions
    Díaz-Requejo, MM
    Pérez, PJ
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) : 5441 - 5450
  • [13] Cyclopropanation versus carbon-hydrogen insertion. The influences of substrate and catalyst on selectivity
    Doyle, MP
    Phillips, IM
    [J]. TETRAHEDRON LETTERS, 2001, 42 (18) : 3155 - 3158
  • [14] Selectivity in reactions of allyl diazoacetates as a function of catalyst and ring size from γ-lactones to macrocyclic lactones
    Doyle, MP
    Hu, WH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) : 8839 - 8847
  • [15] Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis
    Fache, F
    Schulz, E
    Tommasino, ML
    Lemaire, M
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 2159 - 2231
  • [16] FERNANDEZ AI, 2001, CATAL COMMUN, V2, P165
  • [17] The role of binding constants in the efficiency of chiral catalysts immobilized by electrostatic interactions:: The case of azabis(oxazoline)Copper complexes
    Fraile, JM
    García, JI
    Herrerías, CI
    Mayoral, JA
    Reiser, O
    Socuéllamos, A
    Werner, H
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) : 2997 - 3005
  • [18] Theoretical insights into the role of a counterion in copper-catalyzed enantioselective cyclopropanation reactions
    Fraile, JM
    García, JI
    Gil, MJ
    Martínez-Merino, V
    Mayoral, JA
    Salvatella, L
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (03) : 758 - 765
  • [19] Bis(oxazoline)-copper complexes supported by electrostatic interactions:: scope and limitations
    Fraile, JM
    García, JI
    Herrerías, CI
    Mayoral, JA
    Harmer, MA
    [J]. JOURNAL OF CATALYSIS, 2004, 221 (02) : 532 - 540
  • [20] Solvent and counterion effects in the asymmetric cyclopropanation catalysed by bis(oxazoline)-copper complexes
    Fraile, JM
    García, JI
    Mayoral, JA
    Tarnai, T
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 144 (01) : 85 - 89