Table 1 Condition optimization.
From: Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis
Entrya | NHC | Base | Solvent | Yield (%)b | ee (%)c |
|---|---|---|---|---|---|
1d | A | K2CO3 | DCM | nr | – |
2e | A | K2CO3 | DCM | nr | – |
3 | A | K2CO3 | DCM | 75 | – |
4 | B | K2CO3 | DCM | 78 | 84 |
5 | B | Cs2CO3 | DCM | 72 | 79 |
6 | B | DBU | DCM | 70 | 22 |
7 | B | NaOAc | DCM | Trace | – |
8 | B | Et3N | DCM | Trace | – |
9 | B | DIPEA | DCM | Trace | – |
10 | B | DABCO | DCM | 77 | 84 |
11 | B | KHCO3 | DCM | 81 | 83 |
12 | B | K3PO4 | DCM | 52 | 79 |
13 | B | K2CO3 | THF | Trace | – |
14 | B | K2CO3 | DCE | 63 | 87 |
15 | B | K2CO3 | CHCl3 | 75 | 69 |
16 | B | K2CO3 | 1,4-Dioxane | Trace | – |
17f | B | K2CO3 | DCM | 80 | 89 |
18g | B | K2CO3 | DCM | 89 | 93 |
19h | B | K2CO3 | DCM | 85 | 95 |
20h,i | B | K2CO3 | DCM | 82 | 93 |
21h,j | B | K2CO3 | DCM | 80 | 92 |
22h | C | K2CO3 | DCM | 84 | 9 |
23h | – | K2CO3 | DCM | nr | – |
