Table 1. Screen of Chiral Lewis Acids for Enantioselective [2 + 2] Photocycloaddition.
entry | Lewis acid | ligand | yielda (%) | ee (%) |
---|---|---|---|---|
1 | Gd(OTf)3 | 32 | ||
2 | Gd(OTf)3 | 18 | 0 | |
3 | Gd(OTf)3 | 19 | 27 | 0 |
4 | Gd(OTf)3 | 20 | 32 | –6 |
5 | Gd(OTf)3 | 21 | 56 | 21 |
6 | Gd(OTf)3 | 22 | 43 | 56 |
7 | Eu(OTf)3 | 22 | 41 | 78 |
8b | Eu(OTf)3 | 22 | 74 | 85 |
9b,c | Eu(OTf)3 | 22 | 71 | 92 |
Yield determined by 1H NMR using an internal standard.
Using 5 equiv of 16, 5 mol % Ru(bpy)3Cl2, 10 mol % Eu(OTf)3, and 20 mol % ligand 22.
Reaction conducted at −20 °C.