Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-Containing Dipeptides: Improved Stereoinduction under Solvent-Free Conditions

被引:159
作者
Hernandez, Jose G. [1 ]
Juaristi, Eusebio [1 ]
机构
[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico
关键词
SMALL PEPTIDES; CATALYSTS; EFFICIENT; WATER;
D O I
10.1021/jo1022469
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The organocatalytic activity of the methyl ester of (S)-proline-(S)-phenylalanine, (S,S)-2, in the asymmetric aldol reaction between cyclohexanone and acetone with various aromatic aldehydes under solvent-free conditions in a ball mill has been evaluated. alpha,alpha-Dipeptide (S,S)-2 catalyzed the stereoselective formation of the expected aldol products, with higher diastereo- and enantioselectivity relative to similar reactions in solution, up to 91:9 anti:syn diastereomeric ratio and up to 95% enantiomeric excess.
引用
收藏
页码:1464 / 1467
页数:4
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共 31 条
  • [1] Prolinamides versus Prolinethioamides as Recyclable Catalysts in the Enantioselective Solvent-Free Inter- and Intramolecular Aldol Reactions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (16) : 2467 - 2472
  • [2] Highly enantioselective Michael additions in water catalyzed by a PS-Supported pyrrolidine
    Alza, Esther
    Cambeiro, Xacobe C.
    Jimeno, Ciril
    Pericas, Miquel A.
    [J]. ORGANIC LETTERS, 2007, 9 (19) : 3717 - 3720
  • [3] Organocatalytic reactions: effects of ball milling, microwave and ultrasound irradiation
    Bruckmann, Angelika
    Krebs, Anke
    Bolm, Carsten
    [J]. GREEN CHEMISTRY, 2008, 10 (11) : 1131 - 1141
  • [4] Synthesis of proline-derived dipeptides and their catalytic enantioselective direct aldol reactions: catalyst, solvent, additive and temperature effects
    Chen, Y. -H.
    Sung, P. -H.
    Sung, Kuangsen
    [J]. AMINO ACIDS, 2010, 38 (03) : 839 - 845
  • [5] The small peptide-catalyzed direct asymmetric aldol reaction in water
    Dziedzic, P
    Zou, WB
    Háfren, J
    Córdova, A
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) : 38 - 40
  • [6] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES
    EDER, U
    SAUER, G
    WEICHERT, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) : 496 - &
  • [7] Imidazolidinone intermediates in prolinamide-catalyzed aldol reactions
    Fuentes de Arriba, Angel L.
    Simon, Luis
    Raposo, Cesar
    Alcazar, Victoria
    Sanz, Francisca
    Muniz, Francisco M.
    Moran, Joaquin R.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) : 2979 - 2985
  • [8] Water in Stereoselective Organocatalytic Reactions
    Gruttadauria, Michelangelo
    Giacalone, Francesco
    Noto, Renato
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) : 33 - 57
  • [9] ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY
    HAJOS, ZG
    PARRISH, DR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) : 1615 - 1621
  • [10] Green Synthesis of α,β- and β,β-Dipeptides under Solvent-Free Conditions
    Hernandez, Jose G.
    Juaristi, Eusebio
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) : 7107 - 7111