Asymmetric induction of chiral 1,1′-bis(oxazolinyl)ferrocenes as ligands in metal-catalyzed cyclopropanation and Diels-Alder reactions

被引：0
|
作者：
Qiao, Z [1 ]
Shi, XY [1 ]
Bian, QH [1 ]
Hou, SC [1 ]
Wang, M [1 ]
机构：
[1] China Agr Univ, Coll Sci, Beijing 100094, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2004年 / 15卷 / 09期
关键词：
asymmetric induction; 1,1 '-bis(oxazolinyl)ferrocene; ligand; cyclopropanation; Diels-Alder reaction;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Four chiral 1,1'-bis(oxazolinyl)ferrocenes(1a-1d) have been prepared and used as ligands in the copper catalyzed asymmetric cyclopropanation of styrene with ethyl diazoacetate (EDA) and the magnesium catalyzed Diels-Alder reaction between 3-acryloyl-2-oxazolidinone and cyclopentadiene. Enantioselectivities up to 24% and 41%, respectively, for cyclopropanation and Diels-Alder reaction were observed.
引用
收藏
页码：1015 / 1018
页数：4
相关论文
共 50 条
  • [21] Chiral 6,6′-bis(oxazolyl)-1,1′-biphenyls as ligands for copper(I)-catalyzed asymmetric cyclopropanation
    Khanbabaee, Karamali
    Basceken, Sinan
    Florke, Ulrich
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (05) : 831 - 837
  • [22] ASYMMETRIC DIELS-ALDER REACTIONS OF 1,3-DISILOXYCYCLOHEXADIENE WITH CHIRAL ACRYLAMIDES
    LAMYSCHELKENS, H
    GHOSEZ, L
    TETRAHEDRON LETTERS, 1989, 30 (43) : 5891 - 5894
  • [23] Development of Chiral Spiro Ligands for Metal-Catalyzed Asymmetric Reactions
    Bajracharya, Gan B.
    Arai, Midori A.
    Koranne, Priti S.
    Suzuki, Takeyuki
    Takizawa, Shinobu
    Sasai, Hiroaki
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2009, 82 (03) : 285 - 302
  • [24] Development of chiral spiro ligands for metal-catalyzed asymmetric reactions
    Bajracharya, Gan B.
    Arai, Midori A.
    Koranne, Priti S.
    Suzuki, Takeyuki
    Takizawa, Shinobu
    Sasai, Hiroaki
    Bulletin of the Chemical Society of Japan, 2009, 82 (03): : 285 - 302
  • [25] Planar chiral 2-ferrocenyloxazolines and 1,1′-bis(oxazolinyl)ferrocenes-syntheses and applications in asymmetric catalysis
    Sutcliffe, OB
    Bryce, MR
    TETRAHEDRON-ASYMMETRY, 2003, 14 (16) : 2297 - 2325
  • [26] ASYMMETRIC DIELS-ALDER REACTIONS CATALYZED BY A CHIRAL IRON LEWIS-ACID
    KUNDIG, EP
    BOURDIN, B
    BERNARDINELLI, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (18): : 1856 - 1858
  • [27] Chiral Bronsted acid-catalyzed asymmetric aza Diels-Alder reactions
    Akiyama, Takahiko
    Itoh, Junji
    Fuchibe, Kohei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [28] Chiral Anion Directed Asymmetric Carbocation-Catalyzed Diels-Alder Reactions
    Ni, Shengjun
    Naidu, Veluru Ramesh
    Franzen, Johan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (09) : 1708 - 1713
  • [29] Asymmetric diels-alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine
    Corey, E.J. (corey@chemistry.harvard.edu), 1600, American Chemical Society (124):
  • [30] Diels-Alder reactions of oxazolidinone dienophiles catalyzed by zirconocene bis(triflate) catalysts: Mechanism for asymmetric induction
    Jaquith, JB
    Levy, CJ
    Bondar, GV
    Wang, ST
    Collins, S
    ORGANOMETALLICS, 1998, 17 (05) : 914 - 925
12345