Table 2.
Reaction optimization of monocyclic benzyl alcohol involved benzylation reactiona.
| Entry | Ar*CHO | R | Ligand | Time (h) | yield (%)b | ee (%)c |
|---|---|---|---|---|---|---|
| 1 | 3f | Et | dppp | 12 | 26 | 75 |
| 2d | 3f | Et | (R)-L1 | 9 | 60 | 78 |
| 3d | 3a | Et | (S)-L1 | 12 | 51 | 19 |
| 4d | 3a | Et | (R)-L1 | 12 | 60 | 72 |
| 5 | 3f | tBu | (R)-L1 | 9.5 | 83 | 95 |
| 6d | 3f | tBu | dppp | 9.5 | 50 | 83 |
| 7 | rac-3a | tBu | (R)-L1 | 9.5 | 62 | 74 |
aReaction conditions: 1 (0.30 mmol), 2a (0.20 mmol), 3 (0.02 mmol), L1 (0.02 mmol), [Pd(C3H5)Cl]2 (0.01 mmol), TDMAIP (0.28 mmol), and ZnCl2 (0.08 mmol) were stirred in mesitylene (0.5 mL) at 60 °C for indicated time.
bIsolated yield.
cThe enantioselective excess was determined by chiral HPLC.
dWith 10 mol% palladium and 20 mol% (R)-L1.