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. 2017 Apr 19;8(6):4558–4564. doi: 10.1039/c7sc01556a

Table 1. Optimization of reaction conditions a .

Inline graphic
Entry Ligand Solvent Conv b (%) 1a 2a S e
ee c (%) ee c , d (%)
1 L1 THF 64 98 60 17
2 L1 Toluene 71 99 42 11
3 L1 DME 43 63 74 12
4 L1 DCE 44 45 57 5
5 L2 THF 53 92 83 29
6 L3 THF 20 7 50 1
7 L4 THF 21 24 88 25
8 L5 THF 29 38 95 40
9 L6 THF 51 99.4 97 251
10 L7 THF 37 37 64 6
11 L8 THF 39 23 36 3
12 L9 THF 31 5 31 2

aReaction conditions: CuCl (0.025 mmol), ligand (0.025 mmol), rac-1a (0.5 mmol), B2Pin2 (0.6 mmol), MeOK (0.1 mmol), solvent (1.5 mL) MeOH (1.0 mmol), 0 °C, 2 h.

bCalculated conversion, C = ee1a/(ee1a + ee2a).

cDetermined by chiral HPLC and SFC analysis.

dDiastereomeric ratio (dr) > 99 : 1 (determined by 1H NMR).

eSelectivity factor (s) = ln[(1 – C) (1 – ee1a)]/ln[(1 – C) (1 + ee1a)].