Table 1.
Ligand Screen for Asymmetric Hydrogenation of 1aa
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entry | ligand | er (2a) |
1 | (R)-MP2-Segphos | 86.3:13.7 |
2b | (R)-MP2-Segphos | 57.4:42.6 |
3 | (R)-Segphos | 91.8:8.2 |
4 | (R)-MeO-Biphep | 86.4:13.6 |
5 | (R)-Ph-Garphos | 66.5:33.5 |
6 | (R)-Synphos | 89.4:10.6 |
7 | (R)-DTBM-Segphos | 77.5:22.5 |
8 | (R)-Cyclohexyl Soniphos | 84.2:15.8 |
9c | (R)-tBuPHOX | 50.2:49.8 |
10b,d | (R)-tBuPHOX | 53.2:46.8 |
11 | Josiphos-001 | 54.5:45.5 |
12 | Josiphos-003 | 50.2:49.8 |
13b | (S,S)-MeO-BoQphos | 99.3:0.7 |
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Reaction conditions: a mixture of [Ir(COD)Cl]2 and ligand was stirred in a vial for 15 min in 0.75 mL THF, before addition of 25 mg 1a, 100% conv to the desired product unless specified otherwise.
5 mol % of I2 was added to the catalyst solution before addition of substrate.10
33% conv.
40% conv.