Readily available new pyridyl alcohols derived from D-glucose as ligands for the enantioselective addition of diethylzinc to aldehydes

被引:15
作者
Huang, HM [1 ]
Zheng, Z [1 ]
Chen, HL [1 ]
Bai, CM [1 ]
Wang, JW [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(03)00212-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of new chiral ligands derived from D-glucose has been synthesized and applied in the enantioselective addition of diethylzinc to aldehydes. Up to 94.1% e.e. was obtained in the ethylation reactions. In contrast to the ligands derived from D-fructose, ligands derived from D-glucose gave the opposite asymmetric induction. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1285 / 1289
页数:5
相关论文
共 35 条
  • [1] Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)indoline
    Asami, M
    Watanabe, H
    Honda, K
    Inoue, S
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (23) : 4165 - 4173
  • [2] BLASER HU, 1992, CHEM REV, V29, P359
  • [3] CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES
    BOLM, C
    SCHLINGLOFF, G
    HARMS, K
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1191 - 1203
  • [4] OPTICALLY-ACTIVE BIPYRIDINES IN ASYMMETRIC CATALYSIS
    BOLM, C
    ZEHNDER, M
    BUR, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (02): : 205 - 207
  • [5] ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE PYRIDINE-DERIVATIVES AND C-2-SYMMETRICAL 2,2'-BIPYRIDINES
    BOLM, C
    EWALD, M
    FELDER, M
    SCHLINGLOFF, G
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1169 - 1190
  • [6] DIASTEREOISOMERIC PURE 2-(1-HYDROXYALKYL)PYRIDINES AS CATALYSTS IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
    CHELUCCI, G
    SOCCOLINI, F
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (10) : 1235 - 1238
  • [7] Synthesis of new chiral catalysts, pyridyl- and bipyridylalcohols, for the enantioselective addition of diethylzinc to benzaldehyde
    Collomb, P
    von Zelewsky, A
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (21) : 3911 - 3917
  • [8] POLYFUNCTIONAL, STRUCTURALLY DEFINED CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF DIALKYLZINC REAGENTS TO ALDEHYDES
    COREY, EJ
    YUEN, PW
    HANNON, FJ
    WIERDA, DA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) : 784 - 786
  • [9] GOANVIC DL, 2002, TETRAHEDRON-ASYMMETR, V13, P119
  • [10] THE PREPARATION AND PROOF OF STRUCTURE OF 1,2-5,6-DICYCLOHEXYLIDENE-D-GLUCOFURANOSE
    HOCKETT, RC
    MILLER, RE
    SCATTERGOOD, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (09) : 3072 - 3076