Polymer-supported and polymeric chiral guanidines: preparation and application to the asymmetric Michael reaction of iminoacetate with methyl vinyl ketone.
Polymer-supported and polymeric chiral guanidines carrying an imidazolidine skeleton are designed as polymer-based base catalysts. Thus, (R)-2-[(S)-1-hydroxymethyl-2-phenylethylimino]-4-phenylimidazolidine was newly prepared from (R)-phenylglycine as the key functional unit of these guanidines. Application of the polymer-based chiral guanidines to the asymmetric Michael reaction of t-butyl diphenyliminoacetate with MVK led to expected asymmetric induction in the Michael adduct with moderate enantioselectivity in the use of the latter polymeric chiral guanidines.
Wannaporn
Disadee
D
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi, Inage, Chiba, 263-8522, Japan.
Ishikawa
Tsutomu
T
D000085:Acetates / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D006146:Guanidines / Q000138:chemical synthesis / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D008956:Models, Chemical; D011137:Polystyrenes
D000085:Acetates; D002074:Butanones; D006146:Guanidines; D007097:Imines; D007202:Indicators and Reagents; D011137:Polystyrenes; C508278:tert-butyl diphenyliminoacetate; C057920:3-buten-2-one