An efficient and highly enantio- and diastereoselective cyclopropanation of olefins catalyzed by Schiff-base ruthenium(II) complexes

被引:1
|
作者
Miller, JA [1 ]
Jin, WC [1 ]
Nguyen, ST [1 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
D O I
10.1002/1521-3773(20020816)41:16<2953::AID-ANIE2953>3.0.CO;2-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Both electron-rich and electron-deficient olefins - such as styrene and methyl methacrylate - undergo efficient (yields > 90%) cyclopropanation with ethyl diazoacetate as the carbene source to give predominantly trans products with exceptionally high enantioselectivity when the (salen)Ru catalyst shown is used (see scheme).
引用
收藏
页码:2953 / 2956
页数:4
相关论文
共 50 条
  • [1] SCHIFF-BASE COMPLEXES OF RUTHENIUM(II)
    THORNBACK, JR
    WILKINSON, G
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1978, (02): : 110 - 115
  • [2] Highly enantioselective and cis-diastereoselective cyclopropanation of olefins catalyzed by ruthenium complexes of (iminophosphoranyl)ferrocenes
    Hoang, Vo D. M.
    Reddy, Pattubala A. N.
    Kim, Tae-Jeong
    TETRAHEDRON LETTERS, 2007, 48 (45) : 8014 - 8017
  • [3] NOVEL RUTHENIUM(II) SCHIFF-BASE COMPLEXES
    GOPINATHAN, S
    DESHPANDE, SS
    GOPINATHAN, C
    SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1989, 19 (04): : 321 - 337
  • [4] EPOXIDATION OF OLEFINS CATALYZED BY MN(III) SCHIFF-BASE COMPLEXES
    TRIVEDI, BM
    BHATTACHARYA, PK
    GANESHPURE, PA
    SATISH, S
    JOURNAL OF MOLECULAR CATALYSIS, 1992, 75 (02): : 109 - 115
  • [5] Palladium(II)-Catalyzed Enantio- and Diastereoselective Synthesis of Pyrrolidine Derivatives
    Jana, Ranjan
    Pathak, Tejas P.
    Jensen, Katrina H.
    Sigman, Matthew S.
    ORGANIC LETTERS, 2012, 14 (16) : 4074 - 4077
  • [6] Asymmetric cyclopropanation of styrene catalyzed by Cu-(chiral Schiff-base) complexes
    Li, ZN
    Liu, GS
    Zheng, Z
    Chen, HL
    TETRAHEDRON, 2000, 56 (37) : 7187 - 7191
  • [7] EPOXIDATION OF OLEFINS CATALYZED BY FE(III) SCHIFF-BASE COMPLEXES AS CATALYST
    AGARWAL, DD
    BHATNAGAR, RP
    JAIN, R
    SRIVASTAVA, S
    JOURNAL OF MOLECULAR CATALYSIS, 1990, 59 (03): : 385 - 395
  • [8] Cyclopropanation of styrene catalyzed by chitosan Schiff-base copper (II) heterogeneous catalyst
    Sun, W
    Xia, CG
    Wang, AQ
    ACTA CHIMICA SINICA, 2002, 60 (01) : 162 - 165
  • [9] Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes
    Matviitsuk, Anastassia
    Denmark, Scott E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (36) : 12486 - 12490
  • [10] SYNTHESIS AND CHARACTERIZATION OF RUTHENIUM(II) SCHIFF-BASE CARBONYL-COMPLEXES
    KHAN, MMT
    SHAIKH, ZA
    INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 1992, 31 (03): : 191 - 194