Polymer-supported and polymeric chiral guanidines: Preparation and application to the asymmetric Michael reaction of iminoacetate with methyl vinyl ketone

Author:

Wannaporn Disadee,Ishikawa Tsutomu

Publisher

Springer Science and Business Media LLC

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Drug Discovery,Molecular Biology,General Medicine,Information Systems,Catalysis

Reference22 articles.

1. Kirschning, A., Monenschein, H. and Wittenberg, R., Functionalized polymers-emerging versatile tools for solution-phase chemistry and automated parallel synthesis, Angew. Chem. Int. Ed. Engl., 40 (2001) 650–679.

2. Anastas, P. T. and Warner, J. C., Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.

3. Costa, M., Chiusoli, G., Taffurelli, D. and Dalmonego, G., Superbase catalysis of oxazolidin-2-one ring formation from carbondioxide and prop-2-yn-1-amines under homogeneous or heterogeneous conditions, J. Chem. Soc., Perkin Trans, 1, (1998) 1541–1546; Kovacevic, B. and Maksic, Z.B., Basicity of some organic superbases in acetonitrile, Org. Lett., 3 (2001) 1523–1526.

4. Isobe, T., Fukuda, K. and Ishikawa, T., Modified guanidines as potential chiral superbases. 1. Preparation of 1,3-disubstituted 2-iminoimidazolidines and the related guanidiens through chloroamidine derivatives, J. Org. Chem., 65 (2000) 7770–7773; Isobe, T., Fukuda, K., Tokunaga, T., Seki, H., Yamaguchi, K. and Ishikawa, T., Modified guanidines as potential chiral superbases. 2. Preparation of 1,3-unsubstituted and i-substituted 2-iminoimidazolidine derivatives and a related guanidiens by the 2-chloride-induced cyclization of thioureas, J. Org. Chem., 65 (2000) 7774–7778; Isobe, T., Fukuda, K., Tokunaga, T., Seki, H., Yamaguchi, K. and Ishikawa, T., Modified guanidines as potential chiral superbases. 3. Preparation of 1,4,6-triazabicyclooctene systems and 1,4-disubstituted 2-iminoimidazolidines by the 2-chloride-1,3-dimethylimidazolium chloride-induced cyclization of guanidines with a hydroxyethyl substituent, J. Org. Chem., 65 (2000) 7779–7785.

5. Ishikawa, T., Araki, Y., Kumamoto, T., Seki, H., Fukuda, K. and Isobe, T., Modified guanidines as chiral superbases: Application to asymmetric Michael reaction of glycine imine with acrylate or its related compounds, Chem. Commun., (2001) 245–246.

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