Highly enantioselective hydrogenation of α-Alkyl-β-arylpropenoic acids over cinchonidine-modified palladium catalyst

被引:22
|
作者
Sugimura, Takashi [1 ]
Watanabe, Junya [1 ]
Uchida, Takayuki [1 ]
Nitta, Yuriko [1 ]
Okuyama, Tadashi [1 ]
机构
[1] Osaka Univ, Osaka 540, Japan
关键词
asymmetric synthesis; enantioselective hydrogenation; palladium on carbon; olefin;
D O I
10.1007/s10562-006-0159-y
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Enantioselective hydrogenation of (E)- alpha-alkyl-beta-arylpropenoic acids was studied over the cinchonidine-modified Pd/C under the conditions optimized for (E)-alpha,beta-diarylpropenoic acids. Enantiomeric excess (ee) of the product was increased by adjusting the alpha-alkyl group as a properly bulky isopropyl. The ee was as high as 80% when the beta-group is phenyl, and reached 86% with p-anisyl group. Stereoselection of those substrates is similar to that of (E)-alpha,beta-diarylpropenoic acids.
引用
收藏
页码:27 / 30
页数:4
相关论文
共 50 条
  • [21] Activation-temperature dependence in enantioselective hydrogenation of unsaturated carboxylic acids over cinchonidine-modified Pd/C catalysts
    Nitta, Y
    Watanabe, J
    Okuyama, T
    Sugimura, T
    JOURNAL OF CATALYSIS, 2005, 236 (01) : 164 - 167
  • [22] SOLVENT EFFECT ON ENANTIOSELECTIVE HYDROGENATION OF (E)-ALPHA-PHENYLCINNAMIC ACID WITH CINCHONIDINE-MODIFIED PALLADIUM CATALYSTS
    NITTA, Y
    KOBIRO, K
    CHEMISTRY LETTERS, 1995, (02) : 165 - 165
  • [23] Enantioselective hydrogenation of α,β-unsaturated carboxylic acid over cinchonidine-modified Pd nanoparticles confined in carbon nanotubes
    Guan, Zaihong
    Lu, Shengmei
    Li, Can
    JOURNAL OF CATALYSIS, 2014, 311 : 1 - 5
  • [24] Enantioselective hydrogenation of 2-methyl-2-pentenoic acid over cinchonidine-modified Pd/alumina
    Borszeky, K
    Mallat, T
    Baiker, A
    CATALYSIS LETTERS, 1996, 41 (3-4) : 199 - 202
  • [25] Enantioselective hydrogenation of α,β-unsaturated carboxylic acids over cinchonidine modified palladium:: Nature of modifier-reactant interaction
    Borszeky, K
    Bürgi, T
    Zhaohui, Z
    Mallat, T
    Baiker, A
    JOURNAL OF CATALYSIS, 1999, 187 (01) : 160 - 166
  • [26] Reactions of chlorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified Pd: Enantioselective hydrogenation versus hydrodechlorination
    Szollosi, Gyoergy
    Herman, Beata
    Szabados, Erika
    Fueloep, Ferenc
    Bartok, Mihaly
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 333 (1-2) : 28 - 36
  • [27] ENANTIOSELECTIVE HYDROGENATION OF ETHYL PYRUVATE - INFLUENCE OF OXIDATIVE TREATMENT OF CINCHONIDINE-MODIFIED PLATINUM CATALYST AND HEMIKETAL FORMATION IN ALCOHOLIC SOLVENTS
    MINDER, B
    MALLAT, T
    SKRABAL, P
    BAIKER, A
    CATALYSIS LETTERS, 1994, 29 (1-2) : 115 - 124
  • [28] Hydrogenation of 1,2-indanedione over heterogeneous cinchonidine-modified platinum catalysts
    Busygin, Igor
    Rosenholm, Michael
    Toukoniitty, Esa
    Murzin, Dmitry Yu.
    Leino, Reko
    CATALYSIS LETTERS, 2007, 117 (3-4) : 91 - 98
  • [29] Conversion dependence of enantioselective hydrogenation of (E)-alpha-phenylcinnamic acid on cinchonidine-modified Pd/TiO2 catalyst
    Nitta, Y
    Kobiro, K
    CHEMISTRY LETTERS, 1996, (10) : 897 - 898
  • [30] Hydrogenation of 1,2-indanedione over heterogeneous cinchonidine-modified platinum catalysts
    Igor Busygin
    Michael Rosenholm
    Esa Toukoniitty
    Dmitry Yu. Murzin
    Reko Leino
    Catalysis Letters, 2007, 117 : 91 - 98