Table 2. Optimization of the Temperature under the Reaction Conditions Described in Table 1a.
entry | temperature (oC) | time (min) | yield (%)b | ee (%)c |
---|---|---|---|---|
1 | 25 | 5 | 99 | 78 |
2 | 0 | 5 | 99 | 82 |
3 | –20 | 10 | 99 | 87 |
4 | –40 | 15 | 99 | 91 |
5 | –50 | 30 | 99 | 93 |
6 | –79 | 80 | 99 | 92 |
Molar ratio: 13a (0.2 mmol), NCS (0.21 mmol), KF (0.4 mmol), and catalyst 5 (0.5 mol %).
Isolated yields.
The ee values were determined by HPLC analysis using a chiral column Chiralcel OD-H.