Table 5.
Scale up of dynamic kinetic resolution.a
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Entry | 1 (mmol) | Acyl donor | Acyl donor (equiv) | 8 (equiv) | ee (%) | Yield (%)b | ||
0 h | 24 h | 48 h | ||||||
1 | 10 | 7 | 0.75 | 0.35 | — | 2.5 | 97 | 93 (90) |
2 | 10 | 7 | 0.4 | 0.35 | 0.35 | 2.5 | 99 | 91 |
3 | 10 | 6 | 0.75 | 0.35 | — | 1.25 | 98 | (74) |
4c | 45 | 6 | 0.4 | 0.35 | 0.35 | 1.25 | 98 | (68) |
5d | 45 | 6 | 0.75 | 0.35 | — | 1.25 | 98 | (83) |
aConditions: 1, 1.25 mol % of 4, 100 mg of CALB, 200 mg of Na2CO3, acyl donor, hydrogen donor 9, 50 mL of toluene, 100 °C, 72 h; bdetermined by GC, isolated yield in parenthesis; c225 mg of CALB, addition of 113 mg of CALB after 24 and 48 h; d340 mg of CALB, addition of 110 mg of CALB after 24 h.