Table 1. Results from PME and Scale Up Reactions with Diverse Ligands.
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 |
8.6 μmol of 1a at −50 °C.
0.372 mmol of 1a at −78 °C.
Determined by chiral stationary phase (CSP) HPLC.
Conv determined by 1H NMR.
Conducted at −55 °C to simulate PME conditions.