Table 1.
Cycloaddition of the nitrones 20a-20e and allyl alcohol.
| Nitrone | Nucleobase B | Reaction time (h)a,b | cis/trans ratio 21:22 | Yield (%) |
|---|---|---|---|---|
| 20a | 24a 2.5b |
64:36a 69:31b |
21a – 47c; 22a – 28c 21a – 68c; 22a – 25c |
|
| 20b | 15b | 69:31 | 21b–44c; 22b–21c | |
| 20c | 46a 5b |
91:9 91:9 |
21c – 21c; 21c + 22c – 21d 21c – 26c; 21c + 22c – 22d |
|
| 20d | 7.5b | 74:26 | 21d–37c; 21d + 22d–12d; 22d–22c | |
| 20e | ![]() |
5b | 83:17 | 21e – 21c; 21e + 22e – 26d |
The cycloaddition reaction was conducted at 60 °C.
The cycloaddition reaction was conducted under MW irradiation.
Yield of the pure diastereoisomer.
Yield of a pure mixture of diastereoisomers.
