Table 2.
Scope of XtalFluor-E® catalyzed synthesis of N,O-acetals.a
| |||
|---|---|---|---|
|
| |||
| Entry | Enamide | N,O-acetal | Yield (%) |
| 1 |
|
|
95 |
| 2 | 98 | ||
| 3 |
|
|
98 |
| 4 | 95 | ||
| 5 | 80 | ||
| 6 | 40 | ||
| 7 | 98b | ||
| 8 | 85 | ||
| 9 |
|
|
85c |
| 10 |
|
|
98 |
| 11 |
|
|
91 |
| 12 | 72 | ||
| 13 |
|
|
60 |
| 14 |
|
|
98 |
| 15 |
|
|
71 |
| 98d | |||
| 16 |
|
|
83 |
| 17 |
|
|
86 |
| 18 |
|
|
98 |
| 19 |
|
|
98e |
| 21 |
|
|
94 |
| 21 | 98d | ||
Reactions were performed at room temperature (0.1 mmol), reported yields are isolated unless otherwise indicated;
1.1 equivalents of nucleophile was used, requiring 48 h for reaction completion, resulting in the same yield;
Reaction was performed at 1.0 mmol scale;
Yield was determined by 1H-NMR with methyl t-butyl ether as internal standard;
HFIP:methanol (9:1 v:v) was used as solvent.