Recyclable Silica-Supported Proline Sulphonamide Organocatalysts for Asymmetric Direct Aldol Reaction.

Meritxell Ferré, Xavier Cattoën, Michel Wong Chi Man, Roser Pleixats

Research output: Contribution to journalArticleResearchpeer-review

7 Citations (Scopus)

Abstract

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim We describe the preparation of several organosilicas based on proline sulphonamide scaffolds from two chiral monosilylated precursors following sol-gel and grafting procedures. The materials were characterised by using 29Si solid-state NMR spectroscopy, N2 sorption measurements, powder X-ray diffractogram (p-XRD) and elemental analysis. The catalytic performances and reusability of these hybrid silica materials have been evaluated in direct intermolecular asymmetric aldol reactions between ketones and aromatic aldehydes and in a Robinson annulation using simple and green conditions (water, room temperature). Good conversions and recyclability, and from moderate to good diastereo- and enantioselectivities have been achieved. The characteristics of the matrix, and structural features such as the nature and length of the linker, and the derivatisation site on the catalytic organic moiety have an influence on the activity and selectivity of the silica-supported organocatalysts.
Original languageEnglish
Pages (from-to)6741-6748
JournalChemistrySelect
Volume1
Issue number21
DOIs
Publication statusPublished - 1 Jan 2016

Keywords

  • asymmetric aldol reaction
  • catalyst recycling
  • hybrid silica material
  • organocatalysis
  • sol-gel process

Fingerprint

Dive into the research topics of 'Recyclable Silica-Supported Proline Sulphonamide Organocatalysts for Asymmetric Direct Aldol Reaction.'. Together they form a unique fingerprint.

Cite this