Organocatalysis of asymmetric aldol reaction in water: comparison of catalytic properties of (S)-valine and (S)-proline amides

被引:5
作者
Kucherenko, A. S. [1 ]
Siyutkin, D. E. [1 ]
Dashkin, R. R. [2 ]
Zlotin, S. G. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Moscow 125047, Russia
基金
俄罗斯基础研究基金会;
关键词
organocatalysis; asymmetric aldol reaction; (alpha)-amino amides; water; HIGHLY EFFICIENT; PROLINE; KETONES; DIHYDROXYACETONE; ALDEHYDES;
D O I
10.1007/s11172-013-0132-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(S)-Valine amides containing (S)- or (R)-alpha-phenylethyl substituents at N-1 atom efficiently catalyze asymmetric aldol reactions between cyclic (heterocyclic) ketones and aromatic aldehydes in water, predominantly giving rise to the aldol anti-diastereomers in high yields (up to 98%) and enantiomeric excess (up to 94%).
引用
收藏
页码:1010 / 1015
页数:6
相关论文
共 49 条
  • [1] THE USE OF PHOSPHITE AMIDES IN PEPTIDE SYNTHESES
    ANDERSON, GW
    BLODINGER, J
    YOUNG, RW
    WELCHER, AD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (21) : 5304 - 5306
  • [2] Linear TMC-95-based proteasome inhibitors
    Basse, Nicolas
    Piguel, Sandrine
    Papapostolou, David
    Ferrier-Berthelot, Alexandra
    Richy, Nicolas
    Pagano, Maurice
    Sarthou, Pierre
    Sobczak-Thepot, Joeelle
    Reboud-Ravaux, Michele
    Vidal, Joelle
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (12) : 2842 - 2850
  • [3] Bogevig A., 2002, CHEM COMMUN, P620
  • [4] A highly efficient and practical method for catalytic asymmetric vinylogous Mannich (AVM) reactions
    Carswell, Emma L.
    Snapper, Marc L.
    Hoveyda, Amir H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) : 7230 - 7233
  • [5] Chao-Jun L., 2005, CHEM REV, V105, P3095
  • [6] Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes
    Chen, Fubin
    Huang, Shi
    Zhang, Hui
    Liu, Fengying
    Peng, Yungui
    [J]. TETRAHEDRON, 2008, 64 (40) : 9585 - 9591
  • [7] Readily tunable and bifunctional L-prolinamide derivatives: Design and application in the direct enantioselective aldol reactions
    Chen, JR
    Lu, HH
    Li, XY
    Cheng, L
    Wan, J
    Xiao, WJ
    [J]. ORGANIC LETTERS, 2005, 7 (20) : 4543 - 4545
  • [8] Direct catalytic asymmetric cross-aldol reactions in ionic liquid media
    Córdova, A
    [J]. TETRAHEDRON LETTERS, 2004, 45 (20) : 3949 - 3952
  • [9] Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde
    Córdova, A
    Notz, W
    Barbas, CF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) : 301 - 303
  • [10] Recent advances in aldolase-catalyzed asymmetric synthesis
    Dean, Stephen M.
    Greenberg, William A.
    Wong, Chi-Huey
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (8-9) : 1308 - 1320