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. 2021 Oct 4;12(42):14133–14142. doi: 10.1039/d1sc03741b

Performance of select metal triflates in the enantioselective Michael reaction compared to the individual metals' ionic radiia.

graphic file with name d1sc03741b-u1.jpg
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)
a

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.