Table 3.
Enantioselective Synthesis of Tetrahydroquinoxalinesa
| |||||
|---|---|---|---|---|---|
| Entry | Substrate | R1–X | Product | Yield (%)b | er |
| 1 | 3a | Ph–Br | 4a | 79 | 97:3 |
| 2 | 3a | p-PhC(O)-C6H4-Br | 4b | 78 | 96:4 |
| 3 | 3a |
|
4c | 84 | 93:7 |
| 4 | 3a |
|
4d | 82 | 96:4 |
| 5c | 3a |
|
4e | 70 | 93:7 |
| 6 | 3a |
|
4f | 74 | 98:2 |
| 7 | 3b | Ph–Br | 4g | 79 | 96:4 |
| 8 | 3c | Ph–Br | NR | ||
Conditions: 1.0 equiv 3, 2.0 equiv R–X, 2.0 equiv NaOtBu, 2 mol % Pd2(dba)3, 6 mol % (S)-Siphos-PE, toluene (0.1 M), 110 °C, 12-14 h.
Isolated yield (average of two or more runs).
The reaction was conducted at 120 °C in xylenes.
d No reaction was observed.