Chiral pyrrolidine derivatives as catalysts in the enantioselective addition of diethylzinc to aldehydes

被引：61
|
作者：
Yang, XW
Shen, JH
Da, CS
Wang, R [1 ]
Choi, MCK
Yang, LW
Wong, KY
机构：
[1] Lanzhou Univ, Union Lab Asymmetr Synth, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Dept Biol, Lanzhou 730000, Peoples R China
[3] Hong Kong Polytech Univ, Union Lab Asymmetr Synth, Hong Kong, Peoples R China
[4] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 01期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/S0957-4166(98)00497-2
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A series of pyrrolidine derivatives with beta-amino alcohol moieties prepared from (S)-proline were found to catalyze the enantioselective addition of diethylzinc to aldehydes to yield optically active secondary alcohols with high enantioselectivities. A mechanism accounting for the configurational change with the bulkiness of chiral ligands is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：133 / 138
页数：6
相关论文
共 50 条
  • [31] Phenylalanine derivatives as catalysts in the enantioselective addition of diethylzinc to benzaldehydes
    Ionescu, RD
    Blom, A
    Frejd, T
    TETRAHEDRON-ASYMMETRY, 2003, 14 (16) : 2369 - 2380
  • [32] The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes
    Braga, AL
    Rubim, RM
    Schrekker, HS
    Wessjohann, LA
    de Bolster, MWG
    Zeni, G
    Sehnem, JA
    TETRAHEDRON-ASYMMETRY, 2003, 14 (21) : 3291 - 3295
  • [33] CHIRAL QUATERNARY AMMONIUM-SALTS AS SOLID-STATE CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
    SOAI, K
    WATANABE, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) : 43 - 44
  • [34] Enantioselective Addition of Diethylzinc to Aldehydes by Chiral Oxazolidine-Titanium Complex
    Wu, Nan
    Bo, Rongcheng
    Zhang, Rongli
    Jiang, Xi
    Wan, Yu
    Xu, Zhou
    Wu, Hui
    LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (09) : 644 - 649
  • [35] STEREOCONTROLLED ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES USING NEW CHIRAL AMINOALCOHOLS
    KIM, YH
    PARK, DH
    BYUN, IS
    HETEROATOM CHEMISTRY, 1992, 3 (01) : 51 - 54
  • [36] Preparation of Chiral Aminodiols and Their Applications in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes
    Xu, Qian-Yong
    Wu, Tong-Xing
    Pan, Xin-Fu
    Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities, 2002, 23 (07):
  • [37] Design of a Chiral Ionic Liquid System for the Enantioselective Addition of Diethylzinc to Aldehydes
    Bach, Mariana Ferrari
    Griebeler, Cassiana Herzer
    Jacoby, Caroline Gross
    Schneider, Paulo Henrique
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (46) : 6997 - 7004
  • [38] Modular Prolinol Chiral Ligands for Enantioselective Addition of Diethylzinc to Aromatic Aldehydes
    Gou, Shaohua
    Ye, Zhongbin
    Feng, Mingming
    Jiang, Wenchao
    SYNTHETIC COMMUNICATIONS, 2013, 43 (07) : 941 - 950
  • [39] Enantioselective addition of diethylzinc to aldehydes in the presence of chiral hydrazone and imine ligands
    Mino, Takashi
    Suzuki, Atsushi
    Yamashita, Masakazu
    Narita, Shusaku
    Shirae, Yoshiaki
    Sakamoto, Masami
    Fujita, Tsutomu
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (20) : 4297 - 4303
  • [40] Chiral diselenides from benzylamines: Catalysts in the diethylzinc addition to aldehydes
    Wirth, T
    Kulicke, KJ
    Fragale, G
    HELVETICA CHIMICA ACTA, 1996, 79 (07) : 1957 - 1966
12345