Table 1.
| |||
---|---|---|---|
Entry | E+ | Product | Yield |
1 | Mel |
17 |
78% |
2 |
18 |
75% | |
3 |
a)X=Br b)X=1 |
19 |
a) 59% b) 74% |
4 |
a)X=Br b)X=1 |
20 |
a) 52% b) 67% |
5 |
a)X=Br b)X=1 |
21 |
a) 55% b) 69% |
6 | Et3SiCl |
22 |
71% |
7 |
(R)-epichiorohydrin |
(R)-23 |
60% |
Reaction conditions: i) 15, THF, –78° C, then slow addition of nBuLi; ii) electrophile, HMPA, THF, –78° C to –30° C; iii) sat. aq. NH4Cl.