Performance of select metal triflates in the enantioselective Michael reaction compared to the individual metals' ionic radiia.
Entry | Metal ion | r (Å) | Solvent | Time (h) | Yield 6 (%) | ee (%) |
---|---|---|---|---|---|---|
1 | Sc3+ | 0.870 | DCE | 96 | 31 | 90 (S) |
2 | Benzene | 96 | Trace | — | ||
3 | Y3+ | 1.019 | DCE | 18 | 92 | 71 (R) |
4 | Benzene | 18 | 91 | 91 (R) | ||
5 | Dy3+ | 1.027 | DCE | 17 | 88 | 76 (R) |
6 | Benzene | 17 | 83 | 90 (R) | ||
7 | La3+ | 1.160 | DCE | 14 | 93 | 60 (S) |
8 | Benzene | 14 | 97 | 43 (S) |
Conditions: 10 mol% 1 and 5 mol% M(OTf)3 were pre-stirred at 60 °C (1 h). Reactions were performed on 0.15 mmol scale in the listed solvent (0.02 M) at 60 °C for the listed time.