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Cycloaddition Reactions of Deoxyribosylpropynoates |
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| Authors: | Filip Hessler Lucie Kulhavá Ivana Císarˇová Miroslav Otmar |
| Affiliation: | 1. Charles University in Prague, Faculty of Science , Department of Organic Chemistry , Prague , Czech Republic;2. Charles University in Prague, Faculty of Science , Department of Inorganic Chemistry , Prague , Czech Republic;3. Institute of Organic Chemistry and Biochemistry , Academy of Sciences of the Czech Republic , Prague , Czech Republic |
| Abstract: | Pure anomers of either α or β 3-(2-deoxyribofuranosyl)propynoates reacted with the tetramethylcyclobutadiene–aluminum trichloride complex to yield the corresponding diastereoisomeric Dewar benzenes. Thermal- or ultraviolet light–initiated rearrangement gave rise to highly substituted C-aryldeoxyribosides as single anomers. The same compounds as well as other substituted deoxyribosides were obtained also by transition metal–mediated cycloaddition reactions. |
| Keywords: | C-aryldeoxyribosides cycloaddition cyclotrimerization Dewar benzenes unnatural nucleosides |