Table 2. Application scope of the asymmetric epoxidation using amide 6C .
| ||||||
| Entry | R | Ald. | Prod. | Cond. a | Yield b [%] | dr c [%] |
| 1 | Ph | 2a | 17a | A | 78 | >98 |
| 2 | B | 73 | >98 | |||
| 3 | 4-MeC6H4– | 2b | 17b | A | 80 | >98 |
| 4 | 2-MeC6H4– | 2c | 17c | A | 79 | >98 |
| 5 | 4-ClC6H4– | 2d | 17d | A | 75 | >98 |
| 6 | 4-BrC6H4– | 2e | 17e | A | 85 | >98 |
| 7 | 4-PhC6H4– | 2f | 17f | A | 89 | >98 |
| 8 | 4-MeOC6H4– | 2g | 17g | A | 73 | >98 |
| 9 | 4-Me2NC6H4– | 2h | 17h | B | (60) d | >98 |
| 10 | 4-CNC6H4– | 2i | 17i | C | 62 | >98 |
| 11 | 3-NO2C6H4– | 2j | 17j | C | 68 | >98 |
| 12 | n-Decyl– | 2k | 17k | D | 42 | >98 |
| 13 | Cyclohexyl– | 2l | 17l | D | 39 | >98 |
aA: i-PrOH, 25 °C, 24 h, Cs2CO3 (s, 20 eq.); B: toluene, 60 °C, 24 h, Cs2CO3 (s, 20 eq.); C: toluene, 25 °C, 72 h, Cs2CO3 (s, 20 eq.); D: toluene, 25 °C, 24 h, Cs2CO3 (s, 20 eq.).
bIsolated yield.
cDetermined by 1H NMR of the crude reaction mixture.
dFull decomposition on silica gel, crude NMR yield given in brackets.