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Synfacts 2009(6): 0688-0688  
DOI: 10.1055/s-0029-1216761
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Nitro-Michael Addition with Polymer-Supported Organocatalysts

Contributor(s): Yasuhiro Uozumi, Noboru Kobayashi
L. Tuchman-Shukron, M. Portnoy*
Tel Aviv University, Israel
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

Polymer-supported chiral diamine catalysts, such as G0(DPEN), Gn(c-DPEN) (n = 0, 1, 2, carbamate tether), and Gn(u-DPEN) (n = 0, 1, urea tether) were prepared as depicted in equations 1-3. These catalysts promoted the reaction of acetone to trans-β-nitrostyrene to give the Michael adducts in 18-58% yield and 61-82% ee (eq. 4, entries 1-6). After the reaction, G0(c-DPEN) was recovered by filtration and ­reused twice (average 82% ee).