Table 1.
Lipase-catalyzed kinetic resolution of amino ester rac-2 using carbonates 4a–b (ratio 1:2.5) in TBME
| Entry | Enzyme | R | T (°C) | t (h) | eeP (%)a | eeS (%)a | c (%)b | Ec |
|---|---|---|---|---|---|---|---|---|
| 1 | CAL-A Biocatalytics | 3-MeO-C6H4 | 30 | 20 | >99 | 98 | 50 | >200 |
| 2 | CAL-A Roche | 3-MeO-C6H4 | 30 | 8 | >99 | 98 | 50 | >200 |
| 3 | CAL-A Codexis | 3-MeO-C6H4 | 30 | 4 | >99 (92)d | >99 (86)d | 50 | >200 |
| 4 | CAL-B | 3-MeO-C6H4 | 30 | 60 | 99 | 85 | 46 | >200 |
| 5 | CAL-A Codexis | CH2=CHCH2 | 30 | 74 | 92 | 16 | 15 | 29 |
| 6 | CAL-A Codexis | CH2=CHCH2 | 45 | 49 | 94 | 8 | 8 | 35 |
a
Calculated by HPLC
b
c = eeS/(eeS+eep)
c
E = ln[(1−c)×(1−eeP)]/ln[(1−c)×(1+eeP)]
d
Isolated yields in brackets.