Download PDF
Synlett 1990; 1990(4): 201-204
DOI: 10.1055/s-1990-21033
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.

Stereoselective C-C Bond Formation in Carbohydrates by Radical Cyclization Reactions; V. Application for the Synthesis of α-C (2) -Branched Sugars

Alain De Mesmaeker* , Pascale Hoffmann, Tammo Winkler, Adrian Waldner
  • *Central Research Laboratories, Ciba-Geigy Ltd., CH-4002 Basel, Switzerland
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The stereoselectivity of the 5-exo radical cyclization reaction of allylic 2-deoxy-2-iodoglucopyranosides leading to α-C(2)-branched sugars is influenced by the substitution of the allylic double bond. The observed stereoselectivity for the formation of the chiral center on the newly formed tetrahydrofuran ring results from a less sterically hindered transition state of cyclization, except in the case of a cis phenyl substituted C=C double bond.

      >