Table 1.
entry | catalyst | yield (%)b | ee (%)c,d |
---|---|---|---|
1 | none | 0 | - |
2 | Ni(cod)2 (10 mol %), TMEDA (10 mol %) | 0 | - |
3 | Rh(PPh3)3Cl (10 mol %) | <5 | - |
4 | [Rh(C2H4)2Cl]2 (5 mol %), L1 (10 mol %) | 29 | 81 |
5 | [Rh(C2H4)2Cl]2 (5 mol %), L2 (10 mol %) | 56 | 90 |
6 | [Rh(C2H4)2Cl]2 (5 mol %), L3 (10 mol %) | 22 | 79 |
7 | L2 (10 mol %) | 0 | - |
| |||
Conditions: 1 (0.3 mmol), 2 (1.25 equiv), and catalyst in PhMe at 110 °C for 12 h.
Isolated yield.
Enantiomeric excess determined by HPLC using a chiral stationary phase.
Absolute configuration assigned by analogy to (R)-3af (established by X-ray analysis – see SI).