Download PDF
Synlett 2000; 2000(6): 0865-0867
DOI: 10.1055/s-2000-6693
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Indium-Mediated Chain-Extension: An Improved Protocol for the Concise, Diastereospecific Synthesis of KDN and Other Sialic Acids

Mathias Warwel* , Wolf-Dieter Fessner
  • *Darmstadt University of Technology, Department of Organic Chemistry, Petersenstr. 22, 64287 Darmstadt, Germany; Fax +49-6151-166636; E-mail: fessner@tu-darmstadt.de
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Aqueous indium-mediated allylation of d-mannose with ethyl 2-(bromomethyl)acrylate leads, under acidic conditions, exclusively to the threo products in high yields. A new purification procedure for indium-mediated reactions has been developed which is based on a simple precipitation of indium-containing phosphate salts. This simplified protocol leads directly to diastereomerically pure KDN and other sialic acids, thus obviating the need for the usual lengthy purification procedures.

allylation - Barbier-type reactions - diastereoselectivity - indium - stereoselective synthesis