Table 2. α-Alkylation of the 5-(β-Keto)sulfones of Uracil and Cytosine Nucleosidesa.
| entry | substrate | E–Z | product | yield (%)b |
|---|---|---|---|---|
| 1 | 12 | BnBr | 16ac | 50 |
| 2 | 12 | MeI | 17 | 49 |
| 3 | 12 | AllBr | 18 | 46 |
| 4 | 13 | AllBr | 19 | 42 |
| 5 | 14 | BnBr | 20 | 68 |
| 6 | 14 | MeI | 21 | 80 |
| 7 | 15 | BnBr | 22 | 72 |
5-(β-Keto)sulfones 12–15 (0.1 mmol), NaOH/H2O (0.2 mmol)/MeOH, rt, 4–12 h.
Isolated yields.
Also isolated was 16b (17%).
