Table 1.
The reactivity and enantioselectivity of 1•Mb(H64X) and the control MnSalen 1 in catalytic sulfoxidiation at pH= 5.0 and 8.0.a
| Entry | Catalyst | pH=5.0 | pH=8.0 | ||
|---|---|---|---|---|---|
| TON×10−3 min−1b |
e.e.%b | TON×10−3 min−1b |
e.e.%b | ||
| 1 | 1 | 19.5±4.3 | — | 758±74.9 | — |
| 2 | 1•Mb | 405.5±7.8 | 67.0±2.2 | 1654.0±104.3 | 49.8±0.3 |
| 3 | 1•Mb(H64F) | 22.5±3.2 | —c | 597.2 ±33.6 | 38.7± 2.2 |
| 4 | 1•Mb(H64R) | 141.6±10.1 | 43.4±2.1 | 1724.0±184.3 | 47.7±1.1 |
a
Reactions were performed with 5 mM substrate, 10 mM H2O2, 0.5 mM catalyst in 200 μL mixed buffers (50 mM ammonia acetate, Mes, Heps and Tris, pH= 5.0 or 8.0) at 4°C for 10 mins.
b
Yield and enantioselectivity excess (56–60% for 1) were determined by GC with a chiral G-TA column with acetophenone as internal standard and std dev reported in parentheses.
c
For 1•Mb(H64F), in pH 5.0, the reactivity is too low to calculate e.e%.