|
---|
Entry
|
Biocatalyst
|
Time (h)
|
Conversion (%)
a
|
(
R
)-3
b
|
(
S
)-11
b
|
E
c
|
---|
% e.e.
|
% e.e.
|
---|
1 | Lipase AK | 0.5 | >99 | 0 | 0 | -- |
2 | Novozym 435 | 0.5 | 56 | 96 | 97 | 340 |
3 | Lipase PS | 27.5 | 76 | 98 | 32 | 7 |
- Reaction conditions: rac-3 (151 mg, 0.5 mmol), biocatalyst (250 mg, 165% w/w), vinyl acetate (307 μL, 6.6 equiv), n-hexane (5 mL), R.T. aConversion was determined by HPLC (Chiralcel AS-H; flow rate: 0.50 mL/min; iPrOH/n-hexane: 1/99; temperature: 25°C; UV: λ = 199 nm); bthe determination of enantiomeric excess (HPLC chiralcel AS-H) and the absolute configuration (Mosher ester) of 3 are illustrated in Additional file 1; c
E = ln[(1 − e.e.S)(1 − C)]/ln[(1 + e.e.S)(1 − C)], where e.e.S represents the enantiomeric excess of the recovered alcohol.