Table 2.
Entry | Starting materials | GBB product 4 | Yieldb (%) | Cyclized product 6 | Yieldb (%) |
1 |
4b |
94 |
6b |
72 | |
2 |
4c |
80 |
6c |
75 | |
3 |
4d |
62 |
6d |
61 | |
4 |
4e |
96 |
6e |
63 | |
5 |
4f |
89 |
6f |
78 | |
6 |
4g |
61 |
6g |
80 | |
7 |
4h |
85 |
6h |
56 | |
8 |
4i |
88 |
6i |
58 | |
9 |
4j |
64 |
6j |
78 | |
10 |
4k |
75 |
6k |
87 | |
11 |
4l |
49 |
6l |
79 | |
12 |
4m |
71 |
6m |
48 | |
13 |
4n |
47 |
6n |
55 | |
14 |
4o |
54 |
6o |
62 | |
15 |
4p |
95 |
6p |
63 | |
16 |
4q |
74 |
6q |
58 | |
17 |
4r |
43 |
6r |
67 | |
18 |
4s |
57 |
6s |
59 |
aGBB reaction conditions: 1 (0.5 mmol), 2 (0.5 mmol), 3 (0.6 mmol), MeOH (1 mL); PTSA (5%), room temperature, 12h; annulation conditions: substrate 4 (0.2 mmol), Au(JohnPhos)Cl (10 mol %), CH3CN (2 mL) at reflux temperature for 24 h. bIsolated yields.