Synfacts 2008(4): 0427-0427  
DOI: 10.1055/s-2008-1042772
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Aldol Reaction in Water Catalyzed with Polymer-Supported Proline

Contributor(s): Yasuhiro Uozumi, Takao Osako
D. Font, S. Sayalero, A. Bastero, C. Jimeno, M. A. Pericàs*
Institute of Chemical Research of Catalonia, Tarragona and Universitat de Barcelona, Spain
Further Information

Publication History

Publication Date:
19 March 2008 (online)


Polystyrene-support prolines (1-5) were prepared by the cycloaddition of the corresponding azides and alkynes. Prolines 1-5 catalyzed the aldol reaction of cyclohexanone with benzaldehyde in water to give the aldol product 6 in traces to 74% yield with 40-98% ee. When proline 5 was used for the reaction, a gel-like single phase was formed in water. Water-swollen proline 5 showed higher catalytic activity for the aldol reaction of cyclohexanone and 4-nitrobenzaldehyde (99% yield and 96% ee) than anhydrous 5 (80% yield and 89% ee). The aldol reaction of cyclic ketones with various aldehydes was also catalyzed by 5 in water at room temperature to afford the corresponding products in 16-99% yield and 94-99% ee.