Table 1.
| ||
---|---|---|
entrya | additiveb | 23/32: 24c |
1 | — | 66 : 34 |
2 | —d | 39 : 61 |
3 | CuCl2 | 75 : 25 |
4 | ZnCl2 | 41 : 59 |
5 | Cu(OTf)2 | 36 : 64 |
6 | Zn(OTf)2 | 30 : 70 |
7 | 3 Å MS | 32 : 68 |
8 | 4 Å MS | 29 : 71 |
9 | 4 Å MS/Zn(OTf)2 | 27 : 73 |
10 | 4 Å MS/Cu(OTf)2 | 28 : 72 |
Each entry started from pure acetal 23.
Lewis acids were used in 20 mol %; molecular sieves were used in 0.5 g/mmol.
Ratio determined by 1H NMR analysis of crude reaction filtrate after 20–24 h.
At 50 °C.