Table 1.
Condition optimizationa.
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Entry | 1 | 2 | Rh(II) | 6 | 4 or 5 | Yield (%)b | Ee (%)c |
1 | 1a | 2a | Rh2(OAc)4 | rac-6a | 4a | 43 | – |
2 | 1a | 2a | Rh2(OAc)4 | (R)-6b | 4a | 37 | 24 |
3 | 1a | 2a | Rh2(OAc)4 | (R)-6c | 4a | 31 | 12 |
4 | 1a | 2a | Rh2(OAc)4 | (R)-6d | 4a | 47 | 26 |
5 | 1a | 2a | Rh2(OAc)4 | (R)-6e | 4a | 53 | 43 |
6 | 1a | 2a | Rh2(OAc)4 | (R)-6f | 4a | 39 | 8 |
7 | 1a | 2a | Rh2(OAc)4 | (R)-6g | 4a | 45 | 16 |
8 | 1a | 2a | Rh2(OAc)4 | (R)-6h | 4a | 43 | 24 |
9 | 1a | 2a | Rh2(OAc)4 | (R)-6i | 4a | <5 | – |
10 | 1a | 2a | Rh2(OAc)4 | (R)-6j | 4a | 61 | 72 |
11 | 1a | 2a | Rh2(esp)2 | (R)-6j | 4a | 80 | 72 |
12 | 1a | 2b | Rh2(esp)2 | (R)-6j | 5a | 81 | 78 |
13 | 1b | 2b | Rh2(esp)2 | (R)-6j | 5b | 84 | 90 |
14d | 1b | 2b | Rh2(esp)2 | (R)-6j | 5b | 81 | 94 |
15 | 1b | 2b | – | (R)-6j | 5b | <5 | – |
16 | 1b | 2b | Rh2(esp)2 | (R)-6j | 5b | <5 | – |
aAll reactions were run in 0.1 mmol scale of 1, 1:2:3a = 1/1/0.33.
bIsolated yield.
cDetermined by chiral HPLC analysis.
dAt −10 °C.