Table 3.
| ||||
---|---|---|---|---|
entry | scaffold | azide | acid | yield (%) |
1 | 18 | P | 21 | 48 |
2 | 18 | M | 22 | 52 |
3 | 18 | M | 23 | 47 |
4 | 18 | P | 23 | 60 |
5 | 19 | M | 22 | 40 |
6 | 19 | M | 23 | 42 |
7 | 19 | M | 24 | 43 |
Reaction conditions: Isothiazole 1,1-dioxide (40 mg, 1 equiv.), acid (1.2 equiv.), azide (2 equiv.), OACC (1.5 equiv.), CuI (30 mol%), DBU (10 mol%), dry CH2Cl2 (0.2 M), 50 °C, 12 h.
Isolated yields after standard column chromatography (EtOAc, Rf = 0.3–0.6).