Rapid Stereoselective Synthesis of Fluorinated Carbohydrates. Addition of Acetyl Hypofluorite to Vinyl Ether Derivatives of Sugars

摘要

Acetyl hypofluorite has been added to six unsaturated carbohydrates which contain the vinyl ether moiety. All reactions were rapid (less than 5 min.) at -78 degrees C and gave, with one exception, high yields of isomerically pure products. The hypofluorite was shown to add exclusively in a cis mode and with a strong preference for a particular 'face' of the double bond. As well as the syntheses, NMR data and preferred conformations for the fluorinated products are also discussed. (Atomindex citation 15:020515)