|
|---|
|
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.
