ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION

被引:186
|
作者
CHINCHILLA, R [1 ]
NAJERA, C [1 ]
SANCHEZAGULLO, P [1 ]
机构
[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN
关键词
D O I
10.1016/0957-4166(94)80183-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiomerically pure guanidines with and without C-2 symmetry have been prepared and used as catalysts in the addition of nitromethane to aldehydes (Henry reaction). The influence of the structure and amount of the guanidine, the solvent and the temperature in the enantioselectivity of the nitroaldol reaction has also been studied.
引用
收藏
页码:1393 / 1402
页数:10
相关论文
共 50 条
  • [11] Guanidine-thiourea bifunctional organocatalyst for the asymmetric Henry (nitroaldol) reaction
    Sohtome, Y
    Hashimoto, Y
    Nagasawa, K
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1643 - 1648
  • [12] Density functional study on the mechanism of bicyclic guanidine-catalyzed Strecker reaction
    Li, J
    Jiang, WY
    Han, KL
    He, GZ
    Li, C
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23): : 8786 - 8789
  • [13] Preparation of monoglycerides by guanidine-catalyzed processes
    Aguiar, LMG
    Vargas, RM
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1998, 75 (06) : 755 - 756
  • [14] Rate Acceleration of Triethylamine-Mediated Guanidine-Catalyzed Enantioselective Michael Reaction
    Jiang, Zhiyong
    Ye, Weiping
    Yang, Yuanyong
    Tan, Choon-Hong
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) : 2345 - 2351
  • [15] Organocatalytic asymmetric nitroaldol reaction: Cooperative effects of guanidine and thiourea functional groups
    Sohtome, Yoshihiro
    Takemura, Nobuko
    Takada, Keisuke
    Takagi, Rika
    Iguchi, Toshitsugu
    Nagasawa, Kazuo
    CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (09) : 1150 - 1160
  • [16] Asymmetric nitroaldol reaction catalyzed by a chromium(III)-salen system
    Kowalczyk, Rafal
    Sidorowicz, Lukasz
    Skarzewski, Jacek
    TETRAHEDRON-ASYMMETRY, 2007, 18 (21) : 2581 - 2586
  • [17] Chiral bicyclic guanidine-catalyzed enantioselective reactions of anthrones
    Shen, Juan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [18] Recent Progress in Chiral Guanidine-catalyzed Michael Reactions
    Yuan, Jiani
    Li, Minghua
    Ji, Nan
    Liu, Yulong
    He, Wei
    CURRENT ORGANIC CHEMISTRY, 2017, 21 (13) : 1205 - 1226
  • [19] Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines
    Zhang, Yan
    Kee, Choon Wee
    Lee, Richmond
    Fu, Xiao
    Soh, Julian Ying-Teck
    Loh, Esther Mun Foong
    Huang, Kuo-Wei
    Tan, Choon-Hong
    CHEMICAL COMMUNICATIONS, 2011, 47 (13) : 3897 - 3899
  • [20] Chiral bicyclic guanidine-catalyzed enantioselective reactions of anthrones
    Shen, Juan
    Nguyen, Thanh Truc
    Goh, Yong-Peng
    Ye, Weiping
    Fu, Xiao
    Xu, Junye
    Tan, Choon-Hong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (42) : 13692 - 13693