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Synfacts 2011(12): 1375-1375  
DOI: 10.1055/s-0031-1289412
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Solid-Supported Prolinol Ether Catalysts

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Takuma Sato
E. Alza, S. Sayalero, P. Kasaplar, D. Almai, M. A. Pericàs*
Institute of Chemical Research of Catalonia, Tarragona and Universitat de Barcelona, Spain
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

A polystyrene-supported prolinol ether catalyst was developed, which promoted the asymmetric conjugate addition reactions of propionaldehyde with nitroolefins, and dialkyl malonates or nitromethane with cinnamaldehydes with high stereoselectivity. The polymeric catalyst 4 was prepared from proline derivative 1 in three steps through the copper-catalyzed click reaction of an azidomethyl polystyrene resin. The asymmetric reactions were carried out with 10-20 mol% of 4 to give the corresponding products (23 examples; up to >99% ee).