Recoverable silica-gel supported binam-prolinamides as organocatalysts for the enantioselective solvent-free intra- and intermolecular aldol reaction

Abraham Bañón-Caballero, Gabriela Guillena, Carmen Nájera, Enrico Faggi, Rosa María Sebastián, Adelina Vallribera

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36 Citations (Scopus)

Abstract

Silica-gel supported binam-derived prolinamides are efficient organocatalysts for the direct intramolecular and intermolecular aldol reaction under solvent-free conditions using conventional magnetic stirring. These organocatalysts in combination with benzoic acid showed similar results to those obtained under similar homogeneous reaction conditions using an organocatalyst of related structure. For the intermolecular process, the aldol products were obtained at room temperature and using only 2 equiv of the ketone with high yields, regio-, diastereo- and enantioselectivities. Under these reaction conditions, also the cross aldol reaction between aldehydes is possible. The recovered catalyst can be reused up to nine times providing similar results. More interestingly, these heterogeneous organocatalysts can be used in the intramolecular aldol reaction allowing the synthesis of the Wieland-Miescher and ketone analogues with up to 92% ee, with its reused being possible up to five times without detrimental on the obtained results. © 2012 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)1307-1315
JournalTetrahedron
Volume69
Issue number4
DOIs
Publication statusPublished - 28 Jan 2013

Keywords

  • Aldol reaction
  • Enantioselective
  • Organocatalysis
  • Solvent-free
  • Wieland-Miescher ketone

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