Control experiments to elucidate the role of the metal in the fragmentation stepa.
| |||
|---|---|---|---|
| Entry | Added acid | Equiv. | 3b (%) |
| 1 | HCl | 1 | — |
| 2 | AcOH | 1 | — |
| 3 | BF3·Et2O | 0.05 | <5 |
| 4 | BF3·Et2O | 1 | >90 |
| 5 | Sc(OTf)3 | 1 | 29 |
| 6 | PtCl2 | 0.05 | — |
| 7 | [PtCl(dppp)]+ | 0.05 | <5 |
| 8 | 6c | 0.05 | >90 |
All reactions were carried out with 1 mmol of 2b in toluene/H2O 9/1 at 105 °C.
Determined by 1H NMR spectroscopy.