Organobridged silsesquioxanes based on cyclobutane diamines: Influence of the stereochemistry on the morphology of the materials

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Abstract

© 2016 Elsevier Ltd. All rights reserved. Two new organobridged silica-based materials have been prepared by sol-gel hydrolysis-condensation of ureido silyl derivatives of an enantiopure chiral trans 1,2-diaminocyclobutane and an achiral meso 1,2-diaminocyclobutane. The influence of the relative and absolute configuration of the stereogenic centers on the morphology and characterization parameters of the resulting materials has been studied. A right-handed helical shape has been observed for the material obtained starting from the meso-cis diamine whereas the material obtained from the chiral trans diamine showed aggregation in the form of platelets. A preliminary experiment of a reduction of a ketone by hydride transfer reaction catalyzed by a rhodium complex embedded in an organic-inorganic hybrid silica is also reported.
Original languageEnglish
Pages (from-to)2913-2919
JournalTetrahedron
Volume72
Issue number22
DOIs
Publication statusPublished - 2 Jun 2016

Keywords

  • Bridged silsesquioxane
  • Chirality
  • Diaminocyclobutane
  • Hybrid materials
  • Sol-gel process

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