Table 2.
Tested conditions for cyclization precursor 14.
|
| |||
|---|---|---|---|
|
Entry |
Lewis acid |
Conditions |
Product (Yield[a]) |
|
1 |
B(C6F5)3 (2.5 mol%) |
CH2Cl2, 30 °C, 8.5 h |
15 (77 %) |
|
2 |
SnCl4 (1.1 equiv.) |
CH2Cl2, −78 °C to 0 °C, 2 h |
15 (25 %), 16 (19 %) |
|
3 |
SnCl4 (10 mol %) |
CH2Cl2, −78 °C to 0 °C, 4 d |
15 (21 %), 16 (15 %), 14 (36 %) |
|
4 |
SnCl4 (20 mol %) |
CH2Cl2, −78 °C to 0 °C, 2 d |
15 (26 %), 16 (<5 %) |
|
5 |
SnCl4 (30 mol %)[b] |
CH2Cl2, −78 °C to 0 °C, 6 h |
15 (43 %), 16 (1 %) |
|
6 |
SnCl4 (1.1 equiv.) |
toluene, −78 °C to 0 °C, 4 d |
15 (45 %) |
|
7 |
SnCl4 (1.1 equiv.) |
CHCl3, −78 °C to 0 °C, 4 h |
15 (37 %), 16 (<5 %) |
[a] Isolated yield. [b] 0.1 equiv. were added every two hours.