Table 2.
Lipase-catalyzed kinetic resolution of amino esters rac-6a–b using carbonates 4a–b (ratio 1:2.5) in TBME
Entry | Enzyme | R1 | R2 | T (°C) | t (h) | eeP (%)a | eeS (%)a | c (%)b | Ec |
---|---|---|---|---|---|---|---|---|---|
1 | CAL-A Codexis | Me | 3-MeO-C6H4 | 30 | 23.5 | ---- | ---- | 100 | ---- |
2 | CAL-A Codexis | Me | CH2=CHCH2 | 30 | 23 | >99 | 25 | 20 | >200 |
3 | CAL-A Codexis | Me | CH2=CHCH2 | 45 | 48 | >99 | 13 | 12 | >200 |
4 | CAL-A Codexis | Bn | CH2=CHCH2 | 30 | 57 | 88 | >99 | 53 | 121 |
5 | CAL-A Biocatalytics | Bn | CH2=CHCH2 | 30 | 72 | 98 (91)d | >99 (90)d | 50 | >200 |
Calculated by HPLC
c = eeS/(eeS+eep)
E = ln[(1−c)×(1−eeP)]/ln[(1−c)×(1+eeP)]
Isolated yields in brackets.