Table 1.
Kinetic resolution of sulfate esters rac-1 a–7 a with retention and inversion using PAS and PISA1
| Substrate | Enzyme | t [h] | Conv. [%][a] | eeP [%] | eeS [%] | E value[a] |
|---|---|---|---|---|---|---|
| rac-1 a[b] | PAS | 24 | 49 | 97 (S) | 92 (R) | 190 (S) |
| rac-2 a | PAS | 24 | 49 | 91 (S) | 89 (R) | 59 (S) |
| rac-3 a | PAS | 6 | 46 | 98 (S) | 84 (R) | >200 (S) |
| rac-4 a[c | PAS | 6 | 61 | 48 (S) | 74 (R) | 6 (S) |
| rac-5 a[c] | PAS | 6 | 53 | 11 (S) | 11 (R) | <2 (S) |
| rac-6 a[c] | PAS | 6 | 65 | 22 (R) | 40 (S) | ≍2 (R) |
| rac-7 a | PAS | 48 | 30 | >99 (S) | 46 (R) | >200 (S) |
| rac-1 a[b,d] | PISA1 | 6 | 47 | 98 (S) | 89 (S) | >200 (S) |
| rac-2 a[d] | PISA1 | 4 | 56 | 55 (S) | 80 (S) | 8 (S) |
| rac-3 a[d] | PISA1 | 6 | 57 | 32 (S) | 40 (S) | ≍3 (S) |
| rac-4 a[c] | PISA1 | 72 | 50 | >99 (R) | >99 (R) | >200 (R) |
| rac-5 a[c,e] | PISA1 | 24 | 50 | >99 (R) | >99 (R) | >200 (R) |
| rac-6 a[c,d] | PISA1 | 24 | 50 | >99 (R) | >99 (R) | >200 (R) |
| rac-7 a | PISA1 | 72 | 49 | >99 (S) | 93 (S) | >200 (S) |
See the Supporting Information for reaction conditions. [a] Calculated from eeP (ee value of product) and eeS (ee value of starting material) according to Ref. 10c,d. [b] 20 % DMSO (v/v) as cosolvent to suppress non-enzymatic background hydrolysis. [c] Switch in Cahn–Ingold–Prelog priorities. [d] See Ref. 10c. [e] See Ref. 10d.