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
  • [1] Guanidine-catalyzed asymmetric Strecker reaction: modes of activation and origin of stereoselectivity
    Xue, Hansong
    Tan, Choon-Hong
    Wong, Ming Wah
    CANADIAN JOURNAL OF CHEMISTRY, 2016, 94 (12) : 1099 - 1108
  • [2] Copper/Guanidine-Catalyzed Asymmetric Alkynylation of Isatins
    Chen, Quangang
    Tang, Yu
    Huang, Tianyu
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (17) : 5286 - 5289
  • [3] Guanidine-catalyzed asymmetric trimethylsilylcyanation of carbonyl compounds
    Kitani, Y
    Kumamoto, T
    Isobe, T
    Fukuda, K
    Ishikawa, T
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1653 - 1658
  • [4] Guanidine-catalyzed Henry reaction and Knoevenagel condensation
    Han, Junjie
    Xu, Yanfen
    Su, Yingpeng
    She, Xuegong
    Pan, Xinfu
    CATALYSIS COMMUNICATIONS, 2008, 9 (10) : 2077 - 2079
  • [5] Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates
    Yang, Yang
    Dong, Shunxi
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2012, 48 (41) : 5040 - 5042
  • [6] An Unexpected Guanidine-catalyzed Amination Reaction Leading to (Z)-α-Aminocinnamamides
    Bo Jiang
    Tu, Shu-Jiang
    CHEMISTRY LETTERS, 2010, 39 (03) : 210 - 211
  • [7] Guanidine-catalyzed asymmetric addition reactions: Michael reaction of cyclopentenone with dibenzyl malonates and epoxidation of chalcone
    Kumamoto, T
    Ebine, K
    Endo, M
    Araki, Y
    Fushimi, Y
    Miyamoto, I
    Ishikawa, T
    Isobe, T
    Fukuda, K
    HETEROCYCLES, 2005, 66 : 347 - 359
  • [8] Bicyclic Guanidine-Catalyzed Asymmetric Cycloaddition Reaction of Anthrones-Bifunctional Binding Modes and Origin of Stereoselectivity
    Kee, Choon Wee
    Wong, Ming Wah
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23): : 15139 - 15153
  • [9] Copper/guanidine-catalyzed asymmetric alkynylation of isatin-derived ketimines
    Chen, Quangang
    Xie, Lihua
    Li, Zhaojing
    Tang, Yu
    Zhao, Peng
    Lin, Lili
    Feng, Xiaoming
    Liu, Xiaohua
    CHEMICAL COMMUNICATIONS, 2018, 54 (06) : 678 - 681
  • [10] Mechanistic considerations of guanidine-catalyzed reactions
    Fu, Xiao
    Tan, Choon-Hong
    CHEMICAL COMMUNICATIONS, 2011, 47 (29) : 8210 - 8222