DA reaction between 2,3-dimethylbutadiene 7 and various dienophiles.
| |||
|---|---|---|---|
| Entrya | 5 | Conv.b (%) | 8 yieldc (%) |
| 1 | 5a | 82 | 75 |
| 2 | 5b | 100 | 82 |
| 3 | 5c | 80 | 73 |
| 4 | 5d | 32 | 27 |
| 5 | 5e | 7 | 5 |
| 6 | 5f | 16 | 16 |
| 7d | 5f | 34 | 27 |
| 8 | 5g | 61 | 60 |
| 9 | 5h | 100 | 92 |
Reaction conditions: 7 (0.45 M), 5 (0.15 M), C6 and TrX (0.039 M) in 1.1 mL of water-saturated CDCl3, at rt for 16 h.
Determined by 1H NMR analysis of the crude reaction mixture according to literature data.21a,b,26
Isolated yield.
The reaction was carried out at 50 °C.