Table 1. Gold-catalyzed synthesis of 8a: selected optimization a .
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Entry | Acid | Time | Yield b |
1 | 2.1 equiv. MsOH | 24 h | 47% c |
2 | 1.3 equiv. MsOH, 1.1 equiv. TFA | 20 h | 63% |
3 | 1.3 equiv. MsOH, 1.1 equiv. TFA | 6 h | 69% d |
4 | 1.3 equiv. MsOH, 1.1 equiv. TFA | 8 h | 51% e |
5 | 1.3 equiv. MsOH, 1.1 equiv. TFA | 8 h | 74% f |
a[10a] = 0.1 M (0.12 mmol).
bIsolated yield after flash chromatography.
c39% starting material 10a was recovered.
d200 mg scale reaction, 3% AgOTf was added as an additive.
e1 g scale reaction, 5% PPh3AuNTf2, 2% AgOTf as an additive.
f3 g scale reaction, 5% PPh3AuNTf2, 2% AgOTf as an additive, 1 equiv. AgOTf was added with NaHCO3 (s, aq.) to facilitate the cyclization.