Table 1. Effect of the Variation of the Aziridine and Allyl Reagent.
| entry | R | reagent | product | yield (%) |
|---|---|---|---|---|
| 1a,b | CO2tBu | allyl acetate | 12a | 87 |
| 2b,c | COMe | allyl acetate | 12b | 56d |
| 3b,c | CONHEt | allyl acetate | 12c | 60d |
| 4a,b | CN | allyl acetate | 12d | 0e |
| 5d | CO2tBu | none | 13a | 83 |
| 6a | COMe | none | 13b | 82 |
| 7a | CONHEt | none | 13c | 44 |
| 8a | CN | none | 13d | 0e |
| 9a,f | CO2tBu | none | 13a | 0 |
| 10a,g | CO2tBu | none | 13a | 0 |
Reaction performed at 70 °C.
Performed in the presence of 1.3 equiv of K2CO3.
Reaction performed at 30 °C.
Yield determined by 1H NMR using 1,3,5-trimethoxybenzene as the internal standard.
Slow conversion to retro-ene product 3 was observed.9
Performed using Pd(PPh3)4.
Performed using Pd2(dba)3/PPh3.
