Table 1. Catalyst Screeninga.
entry | catalyst | yield (%)b | ee (%)c |
---|---|---|---|
1 | 1 | 99 | 56 |
2 | 2 | 99 | 45 |
3 | 3 | 99 | 50 |
4 | 4 | 99 | 71 |
5 | 5 | 99 | 76 |
6 | 6 | 99 | –75 |
7 | 7 | 99 | 62 |
8 | 8 | 98 | 48 |
9 | 9 | 98 | 51 |
10 | 10 | 98 | 30 |
11 | 11 | 99 | 44 |
12 | 12 | 99 | 47 |
Molar ratio: 13a (0.2 mmol), NCS (0.21 mmol), catalyst 1−12 (0.5 mol %), and KF (0.4 mmol).
Isolated yields.
The ee values were determined by HPLC analysis using a chiral column Chiralcel OD-H.