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
  • [21] Catalytic asymmetric cyclopropanation of electron deficient alkenes mediated by chiral sulfides
    Aggarwal, VK
    Smith, HW
    Jones, RVH
    Fieldhouse, R
    CHEMICAL COMMUNICATIONS, 1997, (18) : 1785 - 1786
  • [22] Rhodium(III)-catalyzed asymmetric carboboration of heterobicyclic alkenes
    Tan, Yun-Xuan
    Liu, Xing-Yu
    He, Cheng-Yu
    Tian, Ping
    TETRAHEDRON, 2021, 77
  • [23] Asymmetric radical cyclopropanation of alkenes
    Lee, Wan-Chen Cindy
    Zhang, X. Peter
    TRENDS IN CHEMISTRY, 2022, 4 (09): : 850 - 851
  • [24] Asymmetric intermolecular cyclopropanation of alkenes by diazoketones catalyzed by Halterman iron porphyrins
    Nicolas, Irene
    Roisnel, Thierry
    Le Maux, Paul
    Simonneaux, Gerard
    TETRAHEDRON LETTERS, 2009, 50 (36) : 5149 - 5151
  • [25] Chromium-Catalyzed Asymmetric Cyclopropanation of Aryl Alkenes with Aryl Dichloromethanes
    Lin, Xiaoyu
    Liu, Houlu
    Yao, Tianbing
    Shen, Haigen
    Wang, Zhaobin
    CHEMCATCHEM, 2025,
  • [26] Steric and electronic effects of substrates and rhodium chiral catalysts in asymmetric cyclopropanation
    Yoshikawa, K
    Achiwa, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (12) : 2048 - 2053
  • [27] Cyclopropanation of alkenes catalyzed by metallophthalocyanines
    Liu, HH
    Wang, Y
    Shu, YJ
    Zhou, XG
    Wu, J
    Yan, SY
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 246 (1-2) : 49 - 52
  • [28] Rhodium-Catalyzed Asymmetric Cyclopropanation of Indoles with N-Triftosylhydrazones
    He, Caicai
    Song, Wei
    Wei, Dandan
    Zhao, Wei
    Yu, Qianfei
    Tang, Jiaqi
    Ning, Yongquan
    Murali, Karunanidhi
    Sivaguru, Paramasivam
    de Ruiter, Graham
    Bi, Xihe
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (50)
  • [29] Chiral Cp-Rhodium(III)-Catalyzed Asymmetric Hydroarylations of 1,1-Disubstituted Alkenes
    Ye, Baihua
    Donets, Pavel A.
    Cramer, Nicolai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) : 507 - 511
  • [30] Rhodium-catalyzed asymmetric intramolecular cyclopropanation of substituted allylic cyanodiazoacetates
    Lin, W
    Charette, AB
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1547 - 1552