An Expedient Method for Kinetically Controlled Acetonide Formation from d-Fructose Induced by Ionic Liquid Catalyst Accompanied with SrCl2 center dot 6H(2)O


YILDIRIM A.

CATALYSIS LETTERS, vol.150, no.9, pp.2566-2571, 2020 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 150 Issue: 9
  • Publication Date: 2020
  • Doi Number: 10.1007/s10562-020-03175-2
  • Title of Journal : CATALYSIS LETTERS
  • Page Numbers: pp.2566-2571
  • Keywords: d-fructose, O-isopropylidenation, Ionic liquid, Chemoselective, Acetonation, O-ISOPROPYLIDENATION, CHIRAL AUXILIARY, ACETONATION, SUGAR, ACID, DERIVATIVES, ACETALS, IODINE

Abstract

The present work was undertaken to ascertain whether IL-metal salt catalyzed isopropylidenation of d-fructose yield desired acetonides. For the first time, an imidazole based ionic liquid compound accompanied with strontium chloride has been identified as a suitable dual catalyst system for the chemoselective O-isopropylidenation of d-fructose with acetone. In the present protocol, mainly the kinetically controlled less stable cyclic ketal 1,2;4,5-di-O-isopropylidene-beta-d-fructopyranose is formed as an initial product with satisfactory yield and without isomerization to the thermodynamically more stable cyclic ketal 2,3;4,5-di-O-isopropylidene-beta-d-fructopyranose. Therefore, this protocol is more advantageous compared to other mineral acid catalyzed protocols that require more sensitive reaction conditions.