| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1313661 | Journal of Fluorine Chemistry | 2015 | 5 Pages |
•Novel fluorinated cyclopropanes have been synthesized by cycloaddition.•The observed π-facial selectivity is determined by the configuration at C-5.•The exo-selectivity was complete in all the cases.
A simple and convenient method for the synthesis of cyclopropanes substituted with carbohydrate analogues is described. The addition of trifluoromethyl diazo compounds to 5-(R)-hydroxypyridazin-3-one derivative of d-(+)-galactose proceeded in almost quantitative yields and high syn-selectivity. The observed π-facial selectivity is determined by the configuration at C-5. The exo-selectivity was complete in all the cases. Steric interactions and electronic factors seem to be the main ones responsible for the observed exo selectivity and π-facial selectivity of reactions with trifluoromethyl diazo compounds.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
