Substrate scope for vinyl azidesa.
| ||||
|---|---|---|---|---|
| Entrya | R3 | Yieldb (%) | drc | eed (%) |
| 1 | 2-MeOC6H4 | 95 (3ab) | >19 : 1 | 92 |
| 2 | 2-ClC6H4 | 91 (3ac) | >19 : 1 | 94 |
| 3 | 3-MeOC6H4 | 90 (3ad) | >19 : 1 | 81 |
| 4 | 3-ClC6H4 | 92 (3ae) | >19 : 1 | 82 |
| 5 | 4-MeC6H4 | 92 (3af) | >19 : 1 | 84 |
| 6 | 4-nBuC6H4 | 91 (3ag) | >19 : 1 | 80 |
| 7 | 4-FC6H4 | 93 (3ah) | >19 : 1 | 95 |
| 8 | 4-ClC6H4 | 87 (3ai) | >19 : 1 | 96 |
| 9 | 4-CO2EtC6H4 | 88 (3aj) | >19 : 1 | 94 |
| 10 | 2-Naphthyl | 95 (3ak) | >19 : 1 | 94 |
| 11 | 3-Thienyl | 85 (3al) | 83 : 17 | 90 |
| 12 | Cyclohexyl | 88 (3am) | >19 : 1 | 95 |
| 13 | Benzyl | 86 (3an) | >19 : 1 | 93 |
a
Unless otherwise noted, all the reactions were carried out with 1a (0.10 mmol), 2 (0.20 mmol) and L3-PiEt2/Ni(BF4)2·6H2O (1 : 1, 10 mol%) in CH2Cl2 (1.0 mL) at 30 °C for 24 h.
b
Isolated yield of 3.
c
Determined by 1H NMR.
d
Determined by HPLC analysis on a chiral stationary phase. Cbz = benzyloxycarbonyl.