Stereoselective C-C Bond Formation in Carbohydrates by Radical Cyclization Reactions; V. Application for the Synthesis of α-C (2) -Branched Sugars
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (04) , 201-204
- https://doi.org/10.1055/s-1990-21033
Abstract
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.Keywords
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