Entry | Ketone | Catalyst | Solvent | Additives | Temp (˚C) | Time (h) | Yield(%)b | dr [syn/anti]c | ee (%)d |
1 | n = 3 | 2 | CH3CN | – | 25 | 48 | 55 | 93:7 | 3 |
2 | n = 3 | 4 | CH3CN | – | 25 | 48 | 40 | 95:5 | 10 |
3 | n = 3 | 4 | CH3CN | – | 5 | 90 | 35 | 95:5 | 15 |
4 | n = 3 | 4 | CH3CN | – | -15 | 144 | 29 | 96:4 | 60 |
5 | n = 3 | 5 | CH3CN | – | 25 | 120 | 86 | 91:9 | 79 |
6 | n = 3 | 5e | CH3CN | – | 25 | 220 | 76 | 90:10 | 77 |
7 | n = 3 | 5 | CH3CN | H2O | 25 | 48 | 61 | 90:10 | 86 |
8 | n = 3 | 5 | CH3CN | AcOH | 25 | 48 | 85 | 89:11 | 88 |
9 | n = 3 | 5 | CH3CN | CF3CO2H | 25 | 104 | 53 | 90:10 | 65 |
10 | n = 3 | 5 | iPrOH | AcOH | 25 | 120 | 63 | 96:4 | 79 |
11 | n = 3 | 5 | iPrOH | AcOH | 5 | 480 | 58 | 93:7 | 85 |
12 | n = 3 | 5 | toluene | – | 25 | 65 | 72 | 90:10 | 87 |
13 | n = 3 | 5 | toluene | AcOH | 25 | 72 | 35 | 89:11 | 89 |
14 | n = 3 | 5 | toluene | H2O | 25 | 48 | 63 | 91:9 | 89 |
15 | n = 3 | 5 | toluene | H2O | 5 | 72 | 87 | 91:9 | 94 |
16 | n = 3 | 5 | neat | – | 25 | 65 | 53 | 95:5 | 85 |
17 | n = 3 | 5 | neat | H2O | 25 | 65 | 84 | 92:8 | 89 |
18 | n = 3 | 5 | neat | H2O | 5 | 72 | 84 | 92:8 | 93 |
19 | n = 3 | 5 | neat | AcOH | 25 | 72 | 35 | 89:11 | 89 |
20 | n = 3 | 6 | neat | – | 25 | 41 | 78 | 92:8 | 84 |
21 | n = 3 | 6 | neat | H2O | 25 | 105 | 93 | 93:7 | 95 |
22 | n = 3 | 6 | neat | AcOH | 25 | 105 | 89 | 93:7 | 95 |
23 | n = 3 | 6 | toluene | – | 25 | 72 | 62 | 91:9 | 87 |
24 | n = 3 | 6 | toluene | AcOH | 25 | 72 | 97 | 93:7 | 86 |
25 | n = 3 | 6 | CH3CN | H2O | 25 | 48 | 93 | 95:5 | 94 |
26 | n = 3 | 6 | CH3CN | H2O | 5 | 60 | 84 | 96:4 | 94 |
27 | n = 3 | 6 | toluene | H2O | 25 | 68 | 86 | 94:6 | 75 |
28 | n = 3 | 6 | toluene | H2O | 5 | 68 | 81 | 96:4 | 98 |
29 | n = 0 | 6 | neat | H2O | 25 | 48 | 74 | - | 25 |
30 | n = 0 | 6 | neat | H2O | 5 | 72 | 68 | - | 29 |