Table 1.
Optimization for Enantioselective Aminocynation
| |||
|---|---|---|---|
| entry | deviations from above conditions | yield (%)a |
ee (%)b |
| 1 | none | 35 | 80 |
| 2 | L1 instead of sBOX(iPr) | 23 | 72 |
| 3 | L2 instead of sBOX(iPr) | 10 | 33 |
| 4 | L3 instead of sBOX(iPr) | 31 | 52 |
| 5 | DCE instead of MeCN | 24 | 71 |
| 6 | EtOAc instead of MeCN | 49 | 69 |
| 7 | Cu(MeCN)4BF4 instead of Cu(OTf)2 | 20 | 74 |
| 8 | 0.05 M | 30 | 75 |
| 9 | 45 °C | 16 | 75 |
| 10 | No Cu(OTf)2 or no Mes-Acr-BF4 or no light | <5 | – |
Reactions were run at 0.2 mmol scale with 2 mL of solvent.
ee was determined by HPLC with chiral stationary phase.