Table 1.
Entry | Pronuelephiles | Base | Product | Yieldb (%) | ||
---|---|---|---|---|---|---|
1d | 1a | LiN(SiMe3)2 | 3aa | 80 | ||
2d | 1a | NaN(SiMe3)2 | 3aa | (99c) | ||
3 | 1a | NaN(SiMe3)2 | 3aa | (99c) | ||
4 | 1c | NaN(SiMe3)2 | 3ca | 27 | ||
5 | 1c | KN(SiMe3)2 | 3ca | 70 | ||
6 | 4a | KN(SiMe3)2 | 5aa | 10 |
Reaction conducted on a 0.1 mmol scale with 1 equiv of pronucleophile and 2 equiv of 2a at 0.1 M.
Yield determined by 1H NMR spectroscopy of the crude reaction mixture.
Isolated yield after chromatographic purification.
1 equiv of NEt3.