Autocatalytic asymmetric reduction of 2,6-diacetylpyridine

被引:5
|
作者
Panosyan, FB [1 ]
Chin, J [1 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
关键词
D O I
10.1021/ol035515k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] We report here that the C-2-symmetric diol 2,6-bis(1-hydroxyethyl)pyridine (2) can effect chiral-catalyzed reduction of 2,6-diacetylpyridine (1) and produce more of the diol (2) with the same configuration in an enantiomerically enriched form. The two carbonyl functionalities of (1) are reduced in 90% conversion to produce the enantio-enriched C-2-symmetric diol (40% ee, 47% de) using zinc trifluoromethanesuffonate and a catalytic amount of the chiral C-2-symmetric diol (2).
引用
收藏
页码:3947 / 3949
页数:3
相关论文
共 50 条
  • [1] CHEMICAL AND STRUCTURAL INVESTIGATIONS ON BISMUTH COMPLEXES OF 2,6-DIACETYLPYRIDINE BIS(2-THENOYLHYDRAZONE) AND 2,6-DIACETYLPYRIDINE BIS(THIOSEMICARBAZONE)
    BATTAGLIA, LP
    CORRADI, AB
    PELIZZI, C
    PELOSI, G
    TARASCONI, P
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1990, (12): : 3857 - 3860
  • [2] A Facile and Efficient Approach to the Synthesis of 2,6-Diacetylpyridine
    Xie, Guangyong
    Ai, Haitao
    Lei, Lu
    Zhang, Dongfang
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2009, 31 (04): : 674 - 676
  • [3] Esterolytic activity of metal complexes, of 2,6-diacetylpyridine dioxime
    Tagle, P. G.
    Yatsimirsky, A. K.
    Polyhedron, 1996, 16 (05)
  • [4] Esterolytic activity of metal complexes of 2,6-diacetylpyridine dioxime
    Tagle, PG
    Yatsimirsky, AK
    POLYHEDRON, 1997, 16 (05) : 877 - 879
  • [5] PREPARATION AND CHARACTERIZATION OF METAL-COMPLEXES OF 2,6-DIACETYLPYRIDINE BIS(IMINES) - CRYSTALLOGRAPHIC STUDY OF DINITRATO[2,6-DIACETYLPYRIDINE BIS(ANIL)]NICKEL(II)
    ALYEA, EC
    FERGUSON, G
    RESTIVO, RJ
    INORGANIC CHEMISTRY, 1975, 14 (10) : 2491 - 2496
  • [6] 2,6-DIACETYLPYRIDINE BIS(ARYLHYDRAZONE) DERIVATIVES AS ANALYTICAL REAGENTS FOR URANIUM
    BONILLAALVAREZ, M
    PALMIERI, M
    DAVIS, D
    FRITZ, JS
    TALANTA, 1987, 34 (05) : 473 - 477
  • [7] NICKEL(II) AND NICKEL(IV) COMPLEXES OF 2,6-DIACETYLPYRIDINE DIOXIME
    BAUCOM, EI
    DRAGO, RS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (24) : 6469 - &
  • [8] TERDENTATE NNN DONOR LIGANDS DERIVED FROM 2,6-DIACETYLPYRIDINE
    ALYEA, EC
    MERRELL, PH
    SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1974, 4 (06): : 535 - 544
  • [9] COPPER(II) COMPLEXES DERIVED FROM 2,6-DIACETYLPYRIDINE DIOXIME
    NICHOLSON, GA
    LAZARUS, CR
    MCCORMICK, BJ
    INORGANIC CHEMISTRY, 1980, 19 (01) : 192 - 195
  • [10] Diaqua[2,6-diacetylpyridine bis(thiosemicarbazone)]manganese(II) diperchlorate
    Othman, AH
    Lee, KL
    Fun, HK
    Yip, BC
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 602 - 605