Subscribe to RSS
Nitro-Michael Addition with Polymer-Supported Organocatalysts
L. Tuchman-Shukron, M. Portnoy*
Tel Aviv University, Israel
25 May 2009 (online)
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).