Table 1.
| ||||
---|---|---|---|---|
entry | catalyst | Et3N (equiv) | % conversion b | % ee c |
1 | (1S,2S)-1 | 0.4 | 100 | 8 |
2 | (R)-5 | — | 0 | — |
3 | (R)-5 | 0.4 | 50 | 4 |
4 | (R)-6 | — | 65 | 5 |
5 | (R)-7 | 0.4 | 100 | 5 |
6 | (R)-8 | 0.4 | 10 | 4 |
7 | (R)-9 | 0.4 | 36 | 0 |
8 | (R)-10 | 0.4 | 100 | 16 |
9 | (R)-11 | 0.4 | 73 | <5 |
10 | (R)-12 | 0.4 | 100 | 74 |
11 | (R,R)-13 | 0.4 | 100 | 6 |
Reactions conducted with 10 equiv CH3NO2 and 20 mol % catalyst in toluene at 25 °C for 12 h except entry 10 which was 2 h.
Determined by 1H NMR spectrum of crude reaction mixture.
Determined by HPLC on Chiralpak OJ-H column.