Optimization of the reaction conditionsa.
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Entry | Cat | n | Ligand | X | Solvent | T/°C | Yieldb (%) | eec (%) |
1 | Nd-1 | 10 | H2L1 | 12 | THF | rt | 99 | 31 |
2 | Nd-1 | 10 | H2L2 | 12 | THF | rt | 99 | 23 |
3 | Nd-1 | 10 | H2L3 | 12 | THF | rt | 86 | 31 |
4 | Nd-1 | 10 | H2L4 | 12 | THF | rt | 99 | 27 |
5 | Nd-1 | 10 | H2L5 | 12 | THF | rt | 99 | 30 |
6 | Nd-1 | 10 | H2L6 | 12 | THF | rt | 99 | 27 |
7 | Nd-1 | 10 | H2L7 | 12 | THF | rt | 86 | 11 |
8 | Nd-1 | 10 | H2L8 | 12 | THF | rt | 99 | 13 |
9 | Nd-1 | 10 | H2L9 | 12 | THF | rt | 99 | 23 |
10 | Sm-2 | 10 | H2L1 | 12 | THF | rt | 99 | 33 |
11 | Eu-3 | 10 | H2L1 | 12 | THF | rt | 89 | 35 |
12 | Yb-4 | 10 | H2L1 | 12 | THF | rt | 35 | 4 |
13 | La-5 | 10 | H2L1 | 12 | THF | rt | 99 | 41 |
14 | La-5 | 10 | H2L1 | 12 | Tol | rt | 99 | 5 |
15 | La-5 | 10 | H2L1 | 12 | Hex | rt | 87 | 37 |
16 | La-5 | 10 | H2L1 | 12 | DME | rt | 89 | 35 |
17 | La-5 | 10 | H2L1 | 12 | CH3CN | rt | 99 | 57 |
18 | La-5 | 10 | H2L1 | 12 | CH3CN | 0 | 99 | 70 |
19 | La-5 | 10 | H2L1 | 12 | CH3CN | -20 | 99 | 80 |
20 | La-5 | 10 | H2L1 | 12 | CH3CN | -40 | 82 | 56 |
21 | La-5 | 10 | H2L1 | 15 | CH3CN | -20 | 99 | 71 |
22 | La-5 | 10 | H2L1 | 20 | CH3CN | -20 | 99 | 75 |
23 | La-5 | 5 | H2L1 | 12 | CH3CN | -20 | 99 | 57 |
The reaction was performed with chalcone (0.3 mmol), TBHP (0.36 mmol) in 1 mL of solvent.
HPLC yield.
Determined by chiral HPLC analysis.