Table 3.
| |||||
---|---|---|---|---|---|
Entry | NuLi | E+ | Quench | Product | Yield |
1 | nBuLi | A |
41 |
68% | |
2 | nBuLi | A |
42 |
69% | |
3 | nBuLi | B |
43 |
72% | |
4 |
44 |
BnBr | B |
45 |
60% |
5 |
44 |
B | 64% | ||
6 |
47 |
B | 67% |
Reaction conditions: i) 15, Et2O, –78 ° C, then slow addition of NuLi; ii) BnBr, HMPA, Et2O, –78 ° C to –30° C; iii) quench A with sat. aq. NH4Cl or quench B with 48 % aq. HF, then NaHCO3.