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. 2018 Aug 27;9(42):8094–8098. doi: 10.1039/c8sc02948b

Table 1. Optimization of the reaction conditions a .

Inline graphic
Entry Variation from standard conditions Yield b (%) ee c (%)
1 0.5 mol% DPZ in CH2Cl2 at 25 °C and without C1 and any additives, 12 h 62 N.A.
2 None 78 93
3 C2 instead of C1 74 76
4 C3 instead of C1 73 67
5 Ru(bpy)3Cl2·6H2O instead of DPZ 58 89
6 Rose Bengal instead of DPZ 69 91
7 No TBPB 76 89
8 No Na2S2O4 75 90
9 No 5 Å MS 76 90
10 No DPZ 35 88
11 No light 0 d N.A.
12 Under air 0 e N.A.
13 No C1 53 N.A.

aReaction conditions: 1a (0.075 mmol), 2a (0.05 mmol), degassed CPME (1.0 mL), 10 °C, irradiation with blue LED (3 W, 450 nm), 36 h.

bYield of the isolated product.

cDetermined by HPLC analysis on a chiral stationary phase.

dNo reaction was detected.

e 1a was consumed, but no 3a was obtained. TBPB = tetra-n-butylphosphonium bromide. CPME = cyclopentyl methyl ether. N.A. = not available.