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. 2014 Mar 25;16(7):1948–1951. doi: 10.1021/ol500506t

Table 1. Results from PME and Scale Up Reactions with Diverse Ligands.

graphic file with name ol-2014-00506t_0008.jpg

      bench scaleb
entry ligand (Figure 1) PMEa ee (%)c conv (%)d ee (%)c
1 BINAP, L1 40 >90 80
2 BINAP, L1   >90 66e
3 H8-BINAP, L2 20 >90 48
4 DACH Trost, L3 0 <10 ND
5 Pfaltz, L4 0 15 14
6 SEGPHOS, L5 42 >90 40
7 DIFLUORPHOS, L6 38 >90 88
8 TUNEPHOS, L7 36 >90 78
9 SONIPHOS, L8 50 >90 72
10 P-PHOS, L9 36 >90 80
11 WALPHOS, L10 36 >90 48
12 MANDYPHOS, L11 34 >90 66
a

8.6 μmol of 1a at −50 °C.

b

0.372 mmol of 1a at −78 °C.

c

Determined by chiral stationary phase (CSP) HPLC.

d

Conv determined by 1H NMR.

e

Conducted at −55 °C to simulate PME conditions.