Table 1. Optimization of the Reaction Conditionsa.
entry | carrot cultivar | additive | time (h) | conv (%)b | yield, erc |
---|---|---|---|---|---|
1 | orange | – | 96 | 46 | – |
2 | yellow | – | 96 | 38 | – |
3 | purple | – | 96 | 66 | – |
4d | purple | TPGS-750-M | 96 | 35 | – |
5d | purple | Triton X-100 | 96 | 18 | – |
6e | purple | buffer pH 6.0, 6.5, 7.0, 7.5 | 96 | 16, 31, 30, 41 | – |
7e | purple | buffer pH 8.0, 8.5, 9.0, 9.5 | 96 | 53, 90, 87, 85 | – |
8 | purple | buffer pH 8.5 | 48 | 62 | – |
9f | purple | buffer pH 8.5 | 48 | 87 | 78%, >99:1 |
General conditions: 14 (50 mg), water (35 mL), EtOH (1 mL), precut carrots (5 g), in Erlenmeyer flask, rt, stirred at 250 rpm.
Conversion was determined by LCMS under 254 nm wavelength.
Enantiomeric ratio was determined by chiral SFC.
2 wt% of additive (0.7 g) was used.
20 mM of 1 M buffer solution (0.7 mL) was applied.
Purple carrots (10 g), isolated yield.