Initial screening of reactions conditions in the presence of a stoichiometric amount of DDQa.
Entry | Method | Acid | Solvent | Temp (°C) | Yieldb (%) |
---|---|---|---|---|---|
1 | A | CH3CN | 25 | NRe | |
2 | A | DCE | 25 | 7 | |
3c | A | DCE | 25 | 11 | |
4 | A | DCE | 80 | 18 | |
5 | B | TFA | DCE | 25 | 10 |
6 | B | TFA | DCE | 80 | 28 |
7 | B | MSA | DCE | 80 | 59 |
8d | B | CBSA | DCE | 80 | 58 |
Reaction conditions: (Method A) (i) 6a (0.15 mmol), DDQ (0.22 mmol), MS 4 Å (20 mg), solvent (0.1 M), rt, 0.5 h; (ii) allyltributyl stannane (0.22 mmol), 24 h. (Method B) (i) 6a (0.37 mmol), DDQ (0.37 mmol), H2O (0.41 mmol), DCE (0.1 M), rt, 24 h; (ii) allyltributyl stannane (0.75 mmol), LiClO4 (0.37 mmol), acid (0.075 mmol), 24 h.
Isolated yield.
LiClO4 (0.5 equiv.) was added.
The reaction mixture was stirred for 6 h before allylstannane was added.
No reaction.