Temperature effect on (Amano PS-IM)-catalyzed KR of rac-4 with vinyl acetate in TBME.
| ||||||
|---|---|---|---|---|---|---|
| Entry | Temp.a (°C) | t (h) | Conv.b (%) | eesc (%) | eepc (%) | E d |
| 1 | 30 | 72 | 55 | >99 | 81 | 49 |
| 2 | 40 | 20 | 52 | 96 | 88 | 61 |
| 3 | 50 | 20 | 56 | >99 | 79 | 44 |
a
Conditions: rac-4 50 mg, Amano PS-IM 25 mg, TBME 1 mL, vinyl acetate 54 mg, 58 μL (3 equiv.), 800 rpm (magnetic stirrer).
b
Based on GC, for confirmation, the % conversion was calculated from the enantiomeric excess of the unreacted alcohol (ees) and the product (eep) according to the formula conv. = ees/(ees + eep).
c
Determined by chiral HPLC analysis.
d
Calculated according to Chen et al.,26 using the equation: E = {ln[(1 − conv.)(1 − ees)]}/{ln[(1 − conv.)(1 + ees)]}.