ASYMMETRIC CYCLOPROPANATION OF ALKENES CATALYZED BY A RHODIUM CHIRAL FORTRESS PORPHYRIN

被引:90
|
作者
OMALLEY, S [1 ]
KODADEK, T [1 ]
机构
[1] UNIV TEXAS,DEPT CHEM & BIOCHEM,AUSTIN,TX 78712
关键词
D O I
10.1021/om00042a052
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
While a number of efficient asymmetric catalysts exist for the cyclopropanation of alkenes by diazo esters, all provide diastereomeric mixtures in which the anti product predominantes. We report here the synthesis and characterization of a chiral rhodium porphyrin catalyst that provides predominantly the syn isomers, with very good diastereoselectivity in some cases. However, the enantioselectivities observed are modest.
引用
收藏
页码:2299 / 2302
页数:4
相关论文
共 50 条
  • [1] ASYMMETRIC CYCLOPROPANATION OF ALKENES CATALYZED BY A CHIRAL WALL PORPHYRIN
    OMALLEY, S
    KODADEK, T
    TETRAHEDRON LETTERS, 1991, 32 (22) : 2445 - 2448
  • [2] MECHANISM OF THE RHODIUM PORPHYRIN CATALYZED CYCLOPROPANATION OF ALKENES
    MAXWELL, JL
    BROWN, KC
    BARTLEY, DW
    KODADEK, T
    SCIENCE, 1992, 256 (5063) : 1544 - 1547
  • [3] Asymmetric Cyclopropanation of Alkenes with Dimethyl Diazomalonate Catalyzed by Chiral Diene-Rhodium Complexes
    Nishimura, Takahiro
    Maeda, Yuko
    Hayashi, Tarnio
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) : 7324 - 7327
  • [4] SHAPE-SELECTIVE AND ASYMMETRIC CYCLOPROPANATION OF ALKENES CATALYZED BY RHODIUM PORPHYRINS
    MAXWELL, JL
    OMALLEY, S
    BROWN, KC
    KODADEK, T
    ORGANOMETALLICS, 1992, 11 (02) : 645 - 652
  • [5] Transition-state model for the rhodium porphyrin-catalyzed cyclopropanation of alkenes by diazo esters
    Brown, Kathylynn C.
    Kodadek, Thomas
    Journal of the American Chemical Society, 1992, 114 (21):
  • [6] A TRANSITION-STATE MODEL FOR THE RHODIUM PORPHYRIN-CATALYZED CYCLOPROPANATION OF ALKENES BY DIAZO ESTERS
    BROWN, KC
    KODADEK, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8336 - 8338
  • [7] Asymmetric epoxidation of alkenes catalyzed by novel chiral porphyrin metal complexes
    Sakthipriya, Pachiannan
    Ananthi, Nallamuthu
    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2016, 20 (06) : 730 - 737
  • [8] Asymmetric cyclopropanation of alkenes and diazocarbonyl insertion into S-H bonds catalyzed by a chiral porphyrin Ru(II) complex.
    Galardon, E
    Roué, S
    Le Maux, P
    Simonneaux, G
    TETRAHEDRON LETTERS, 1998, 39 (16) : 2333 - 2334
  • [9] Ruthenium(II) porphyrin catalyzed cyclopropanation of alkenes with tosylhydrazones
    Zhang, JL
    Chan, PWH
    Che, CM
    TETRAHEDRON LETTERS, 2003, 44 (48) : 8733 - 8737
  • [10] Rhodium-catalyzed cyclopropanation of alkenes with dimethyl diazomalonate
    Gonzalez-Bobes, Francisco
    Fenster, Michael D. B.
    Kiau, Susanne
    Kolla, Laxma
    Kolotuchin, Sergei
    Soumeillant, Maxime
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (06) : 813 - 816