Synthesis of new chiral [2-(1-hydroxyalkyl)pyrrolidino]methylferrocenes and application to the catalytic asymmetric addition of diethylzinc to arylaldehydes

被引:5
|
作者
Xu, CL [1 ]
Wang, MC [1 ]
Hou, XH [1 ]
Liu, HM [1 ]
Wang, DH [1 ]
机构
[1] Zhengzhou Univ, Dept Chem, Zhengzhou 450052, Peoples R China
关键词
chiral [2-(1-hydroxyalkyl)pyrrolidino]methylferrocene; synthesis; asymmetric addition; diethylzinc; arylaldehyde;
D O I
10.1002/cjoc.200591443
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of new optically active [2-(1-hydroxyalkyl)pyrrolidino]methylferrocenes were conveniently prepared from commercially available L-proline and ferrocenecarboxylic acid. The crystal structure of key intermediate was obtained. They were then applied to catalyze enantioselective addition of diethylzinc to arylaldehydes with enantioselectivity up to 99%. The effects of the ligand structures on the enantioselectivity were also studied.
引用
收藏
页码:1443 / 1448
页数:6
相关论文
共 50 条
  • [1] Synthesis of Novel Chiral Pyrimidone Salts and their Application in Asymmetric Diethylzinc Addition of Arylaldehydes
    Zhou, Bi-Hui
    He, Wei-Ping
    Li, Lin-Lin
    Fan, Li-Mei
    Li, Xiang-Rong
    Li, Jie
    CURRENT ORGANIC SYNTHESIS, 2018, 15 (01) : 137 - 142
  • [2] CATALYTIC ASYMMETRIC-SYNTHESIS OF CHIRAL DIOL, BIS[2-(1-HYDROXYALKYL)-PHENYL]ETHER, AN ASYMMETRIC AUTOCATALYTIC REACTION
    SOAI, K
    HAYASE, T
    SHIMADA, C
    ISOBE, K
    TETRAHEDRON-ASYMMETRY, 1994, 5 (05) : 789 - 792
  • [3] DIASTEREOISOMERIC PURE 2-(1-HYDROXYALKYL)PYRIDINES AS CATALYSTS IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
    CHELUCCI, G
    SOCCOLINI, F
    TETRAHEDRON-ASYMMETRY, 1992, 3 (10) : 1235 - 1238
  • [4] A new class of C2 chiral photodimer ligands for catalytic enantioselective diethylzinc addition to arylaldehydes
    Ueda, Yuki
    Yagishita, Fumitoshi
    Ishikawa, Hiroki
    Kaji, Yuki
    Baba, Nozomi
    Kasashima, Yoshio
    Mino, Takashi
    Sakamoto, Masami
    TETRAHEDRON, 2015, 71 (36) : 6254 - 6258
  • [5] A SIMPLE SYNTHESIS OF 2-(1-HYDROXYALKYL)ACRYLONITRILES
    BASAVAIAH, D
    GOWRISWARI, VVL
    SYNTHETIC COMMUNICATIONS, 1987, 17 (05) : 587 - 591
  • [6] Synthesis of New C2-Symmetric Six-Membered NHCs and Their Application for the Asymmetric Diethylzinc Addition of Arylaldehydes
    Li, Jie
    Zhou, Bihui
    Jiang, Yajie
    Liu, Xiaoming
    CATALYSTS, 2018, 8 (02)
  • [7] Chiral ligand 2-(2′-piperidinyl)pyridine:: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes
    Cheng, Yan-Qin
    Bian, Zheng
    Kang, Chuan-Qing
    Guo, Hai-Quan
    Gao, Lian-Xun
    TETRAHEDRON-ASYMMETRY, 2008, 19 (13) : 1572 - 1575
  • [8] Chiral salen-aluminum complex as a catalyst for enantioselective α-addition of isocyanides to aldehydes:: Asymmetric synthesis of 2-(1-hydroxyalkyl)-5-aminooxazoles
    Wang, Shi-Xin
    Wang, Mei-Xiang
    Wang, De-Xian
    Zhu, Jieping
    ORGANIC LETTERS, 2007, 9 (18) : 3615 - 3618
  • [9] SYNTHESIS OF NEW CHIRAL CATALYSTS, N-ALKYL-2-AZANORBORNYL-METHANOLS, FOR THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ARYLALDEHYDES
    NAKANO, H
    KUMAGAI, N
    KABUTO, C
    MATSUZAKI, H
    HONGO, H
    TETRAHEDRON-ASYMMETRY, 1995, 6 (06) : 1233 - 1236
  • [10] SYNTHESIS OF 2-(1-HYDROXYALKYL)ACRYLONITRILES BY THE COCATALYSIS OF A BASE AND AN ACID
    IMAGAWA, T
    UEMURA, K
    NAGAI, Z
    KAWANISI, M
    SYNTHETIC COMMUNICATIONS, 1984, 14 (13) : 1267 - 1273