Baker's yeast reduction of (E)-1-phenyl-1,2-propanedione 2-(O-methyloxime). A key step for a (-)-norephedrine synthesis

被引：36
|
作者：
Kreutz, OC [1 ]
Moran, PJS [1 ]
Rodrigues, JAR [1 ]
机构：
[1] UNIV ESTADUAL CAMPINAS,INST QUIM,BR-13081970 CAMPINAS,SP,BRAZIL
来源：
TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 15期
基金：
巴西圣保罗研究基金会;
关键词：
D O I：
10.1016/S0957-4166(97)00280-2
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The enantioselective Baker's yeast reduction of (E)-1-phenyl-1,2 propanedione 2-(O-methyloxime) 1 afforded (-)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime) 2 with 97% of enantiomeric excess (ee) which was diastereoselectively reduced by LiAlH4 to obtain the (-)-(R,S)-norephedrine with ee=82% and (-)-(R,R)-norpseudoephedrine with ee=93% in a ratio 4:1 respectively. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：2649 / 2653
页数：5
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  • [1] Baker's yeast reduction of (E)-1-phenyl-1,2-propanedione 2-(O-methyloxime). A key step for a (-)-norephedrine synthesis
    [J]. Tetrahedron Asymmetry, 15 (2649):
  • [2] Enantioselective bioreduction of (E)-1-phenyl-1,2-alkanedione 2-(O-methyloxime)
    Kreutz, OC
    Segura, RCM
    Rodrigues, JAR
    Moran, PJS
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (10) : 2107 - 2115
  • [3] PREPARATION OF (-)-(1R,2S)-1-PHENYLPROPANE-1,2-DIOL BY FERMENTING BAKER YEAST REDUCTION OF 1-PHENYL-1,2-PROPANEDIONE
    BRENELLI, ECS
    MORAN, PJS
    RODRIGUES, JAR
    [J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (02) : 261 - 266
  • [4] Preparation of an (-)-ephedrine intermediate through asymmetric reduction of 1-phenyl-1,2-propanedione by anaerobically pre-treated baker's yeast
    Lourenço, E
    Rodrigues, JAR
    Moran, PJS
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 29 (1-6) : 37 - 40
  • [5] The effect of oxygen and the reduction temperature of the Pt/Al2O3 catalyst in enantioselective hydrogenation of 1-phenyl-1,2-propanedione
    Toukoniitty, E
    Mäki-Arvela, P
    Villela, AN
    Neyestanaki, AK
    Salmi, T
    Leino, R
    Sjöholm, R
    Laine, E
    Väyrynen, J
    Ollonqvist, T
    Kooyman, PJ
    [J]. CATALYSIS TODAY, 2000, 60 (3-4) : 175 - 184
  • [6] Modeling of the enantioselective hydrogenation of 1-phenyl-1,2-propanedione over Pt/Al2O3 catalyst
    Toukoniitty, E
    Mäki-Arvela, P
    Wärnå, J
    Salmi, T
    [J]. CATALYSIS TODAY, 2001, 66 (2-4) : 411 - 417
  • [7] Enantioselective hydrogenation of 1-phenyl-1,2-propanedione over Pt on immobilized cinchonidine on γ-Al2O3 catalysts
    Campos, Cristian H.
    Torres, Cecilia
    Fierro, Jose L. G.
    Reyes, Patricio
    [J]. APPLIED CATALYSIS A-GENERAL, 2013, 466 : 198 - 207
  • [8] Interaction of cinchonidine and 1-phenyl-1,2-propanedione on the surface of a chirally modified Pt/Al2O3 hydrogenation catalyst
    Busygin, Igor
    Tkachenko, Olga P.
    Nieminen, Ville
    Borovkov, Victor Yu.
    Sillanpaeae, Reijo
    Toukoniitty, Esa
    Kustov, Leonid M.
    Murzin, Dmitry Yu.
    Leino, Reko
    [J]. JOURNAL OF PHYSICAL CHEMISTRY C, 2007, 111 (26): : 9374 - 9383
  • [9] Synthesis and Crystal Structures of 1-(3-{[(E)-3,5-Dibromo-2-hydroxybenzylidene]amino}phenyl)ethanone O-methyloxime
    Ren, Zong-Li
    Yang, Cheng-Juan
    Lu, Rui-E
    Li, Xin-Ran
    [J]. ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (16) : 5113 - 5115
  • [10] STRUCTURE AND ABSOLUTE-CONFIGURATION OF (+)589-(2-CYANOETHYL)BIS[(E,E)-1-PHENYL-1,2-PROPANEDIONE DIOXIMATO-N,N'](PYRIDINE)COBALT(III), [CO(C3H4N)(C9H9N2O2)2(C5H5N)]
    UCHIDA, A
    OHASHI, Y
    SASADA, Y
    OHGO, Y
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1985, 41 (JAN) : 25 - 26
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