The design, the synthesis and the successful immobilization of a modified Takemoto's catalyst is described. As support, poly(methylhydrosiloxane (PMHS) was chosen for its several positive features: it is a cheap, commercially available polymer, easily functionalized with simple experimental procedures. The PMHS-anchored enantiomerically pure bifunctional organocatalyst was employed in the stereoselective addition of activated carbon nucleophiles to nitrostyrene and its recovery and recyclability was preliminarily investigated.
Review: A. F. Trindade, C. A. M. Afonso, Chem. Rev. 2009, 109, 3401-3429.
a) M. Benaglia, Ed. Recoverable and Recyclable Catalysts 2009, John Wiley and Sons; b) N. Haraguchi, S. Itsuno, Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis 2011, John Wiley & Sons.
For a review on PMHS see: N.J. Lawrence, M.D. Drew, S.M. Bushell, J. Chem. Soc. Perkin Trans 1 1999, 3381-3391. For recent contributions see J. Gajewy, J. Gawronski, M. Kwit, Org. Biomol. Chem. 2011, 9, 3863-3870 and references cited.
Financed by the National Centre for Research and Development under grant No. SP/I/1/77065/10 by the strategic scientific research and experimental development program:
SYNAT - “Interdisciplinary System for Interactive Scientific and Scientific-Technical Information”.