Table 2. Optimization of the Cycloisomerization of 4aa.

| entry | catalyst | solvent | t (min) | yield (%)b |
|---|---|---|---|---|
| 1 | PPh3AuCl/AgNTf2 | toluene | 60 | –c |
| 2 | AgNTf2 | toluene | 30 | 79 |
| 3 | AgNTf2 | THF | >240 | –c |
| 4 | AgNO3 | toluene | 40 | 91 |
| 5 | Ag2CO3 | toluene | 40 | 97 |
| 6 | AgOAc | toluene | 40 | 94 |
| 7 | AgOTf | toluene | 50 | 91 |
| 8 | AgSbF6 | toluene | 30 | 91 |
| 9 | CuI | toluene | >1 d | traces |
| 10 | PtCl2 | toluene | >1 d | traces |
| 11 | Ag2CO3 | toluene/THF 4:1 | 4 h | 94 |
| 12d | Ag2CO3 | toluene | 40 | 97 |
Reaction conditions: 0.13 mmol of 3a, 10 mol % of catalyst, 1.3 mL solvent, rt.
Yield of isolated 4a after flash column chromatography.
Complicated mixture of products which could not be separated.
In the presence of 20 mol % A and 40 mol % (S)-N-Boc alanine.