Table 3.
Aza-[3 + 3] annulations of 17-cis.
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entrya | HX (1.0 equiv) | solvent | temp (°C) | time (h) | yield (%)b |
1 | HOAc | EtOAc | 25 | 18 | – |
2 | HOAc | EtOAc | 85 | 12 | 17-trans |
3 | HO2CCF3 | EtOAc | 55 | 12 | 17-trans |
4 | HO2CCF3 | EtOAc | 130 | 12 | decomp |
5 | HO2CCF3 | toluene | 100 | 5 | 30% of 26 |
aAll reactions run in a sealed tube. Concn = 0.03–0.04 M; 5.0 equiv Na2SO4. bIsolated yields.