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. 2016 Aug 9;49(10):2307–2315. doi: 10.1021/acs.accounts.6b00280

Table 1. Screen of Chiral Lewis Acids for Enantioselective [2 + 2] Photocycloaddition.

graphic file with name ar-2016-00280n_0009.jpg

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
a

Yield determined by 1H NMR using an internal standard.

b

Using 5 equiv of 16, 5 mol % Ru(bpy)3Cl2, 10 mol % Eu(OTf)3, and 20 mol % ligand 22.

c

Reaction conducted at −20 °C.