Table 7.
CAL‐B‐catalyzed preparative‐scale resolution of (±)‐7–(±)‐9 [a].
| Alcohol recovered | Ester produced | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| [(R)‐7–(R)‐9] | [(S)‐10–(S)‐12] | ||||||||
| Entry | Substrate | Time [h] | Conv. [%] | Yield [%] | ee [b] [%] | [α]D 25 | Yield [%] | ee [b] [%] | [α]D 25 |
| 1 | (±)‐7 | 1.5 | 50 | 47 | 98 | +107.5[c] | 46 | 98 | −102.2[d] |
| 2 | (±)‐8 | 2.5 | 50 | 47 | 98 | +82[e] | 43 | 98 | −92.3[f] |
| 3 | (±)‐9 | 2 | 49 | 47 | 96 | +97[g] | 45 | 98 | −131.8[h] |
[a] Toluene, with acetic anhydride, at 60 °C. [b] According to HPLC. [c] c=0.34 in EtOH. [d] c=0.32 in EtOH. [e] c=0.23 in EtOH. [f] c=0.61 in EtOH. [g] c=0.21 in EtOH. [h] c=0.38 in EtOH.