Optimization of a sequential one-pot process with PDMS thimble.
Entry | Chamber | rac-1a [mmol] | Mn oxidant [g] | CH2Cl2 [mL] | Enzyme [U mmol−1] | NADP+ [μmol] | Buffer [mL] | IPA [mL] | Yielda [%] (eeb) | |
---|---|---|---|---|---|---|---|---|---|---|
2a | (R)-1a | |||||||||
1 | Interior | 1 | 2 | 4 | — | — | — | — | 19 | 4 (93% ee) |
Exterior | — | — | — | 120 | 20 | 15 | 5 | 42 | 31 (>99% ee) | |
2 | Interior | 1 | 2 | 4 | — | — | — | — | n.d.c | n.d.c |
Exterior | — | — | — | 120 | 20 | 15 | 15 | 35 | 57 (>99% ee) | |
3 | Interior | 1 | 2 | 4 | — | — | — | — | n.d.c | n.d.c |
Exterior | — | — | — | 500 | 20 | 15 | 15 | 13 | 86 (>99% ee) | |
4 | Interior | 1 | 0.5 | 4 | — | — | — | — | n.d.c | n.d.c |
Exterior | — | — | — | 500 | 20 | 15 | 15 | 3 | 95 (>64% ee) | |
5 | Interior | 1 | 1 | 4 | — | — | — | — | n.d.c | n.d.c |
Exterior | — | — | — | 500 | 20 | 15 | 15 | 4 | 96 (>99% ee) | |
6 | Interior | 1 | 1.5 | 4 | — | — | — | — | n.d.c | n.d.c |
Exterior | — | — | — | 500 | 20 | 15 | 15 | 6 | 91 (>99% ee) | |
7 | Interior | 1 | 3 | 4 | — | — | — | — | n.d.c | n.d.c |
Exterior | — | — | — | 500 | 20 | 15 | 15 | 14 | 84 (>99% ee) |
Yield was calculated from 1H-NMR.
Enantiomeric excess of (R)-1-phenylethanol was determined by chiral HPLC.
n.d.: not detected.