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2012 | 1 | 1-5

Article title

Poly(methylhydrosiloxane)-supported chiral thiourea-based bifunctional catalysts


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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.







Physical description


23 - 8 - 2012


  • Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133, Milano, Italy
  • Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133, Milano, Italy
  • Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133, Milano, Italy
  • Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Mangiagalli 25, 20133, Milano, Italy


  • 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.
  • M. S. Bratcher, M. S. DeClue, A. Grunnet-Jepsen, D. Wright, B. R. Smith, W. E. Moerner, J. S. Siegel, J. Am. Chem. Soc. 1998, 120, 9680-9681.
  • M. Benaglia, A. Puglisi, F. Cozzi, Chem. Rev. 2003, 103, 3401-3429. See also F. Cozzi, Adv. Synth. Catal. 2006, 348, 1367-1390.
  • M. S. DeClue, J. S. Siegel, Org. Biomol. Chem. 2004, 2, 2287-2298.
  • S. Guizzetti, M. Benaglia, J. S. Siegel, Chem. Comm. 2012, 3188-3190.
  • A. Puglisi, M. Benaglia, R. Annunziata, J. S. Siegel, Chem. Cat. Chem. 2012, 4, 972-975.
  • Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299-4321.
  • M. Kaik, J. Gawronski, Tetrahedron Asymmetry 2003, 14, 1559-1563.
  • Typically supported catalyst 9 with a 1:1 x/y ratio was employed in catalytic experiments; the use of polymers with different x/y ratio did not bring any appreciable variation in the stereochemical efficiency of the catalytic system.

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