Screening of solventsa.
| ||||
|---|---|---|---|---|
| Entry | Solvent | Time | Yieldb (%) | eec (%) |
| 1 | n-Hexane | 24 | 52 | 48 |
| 2 | Toluene | 72 | 49 | 45 |
| 3 | CH2Cl2 | 72 | 41 | 30 |
| 4 | EtOAc | 24 | 67 | 54 |
| 5 | CH3OCH2CH2OCH3 | 36 | 47 | 40 |
| 7 | MTBE | 36 | 84 | 49 |
| 8 | THF | 36 | 81 | 69 |
| 9 | Dioxane | 36 | 76 | 57 |
| 10 | MeOH | 24 | 69 | 57 |
| 11 | Ethylene glycol | 24 | 42 | 57 |
Reaction conditions: the azodicarboxylate (1 equiv.) was added to the aldehyde (1.5 equiv.), with catalyst (15 mol%) in THF at rt for the stated period of time under argon. Reaction without isolation of intermediate.
Isolated yield.
Determined by chiral HPLC.