Table 1.
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Entry | Catalyst | Solvent | Timeb (h) | Ratio 1a/2a | Yieldc (%) of 6a |
1 | 3a | CH2Cl2 | 4.5 | 1:1 | – d |
2 | 3a | CHCl3 | 4.5 | 1:1 | – d |
3 | 3a | toluene | 4.5 | 1:1 | – d |
4 | 3a | DMSO | 4.5 | 1:1 | 10 |
5 | 3a | MeOH | 4.5 | 1:1 | 51 |
6 | 3a | EtOH | 4.5 | 1:1 | 50 |
7 | 3b | EtOH | 4.5 | 1:1 | 10 |
8 | 3c | EtOH | 4.5 | 1:1 | – |
9 | 3d | EtOH | 4.5 | 1:1 | – |
10 | 3a | EtOH | 3 | 1:1 | 42 |
11 | 3a | EtOH | 8 | 1:1 | 46 |
12 | 3a | EtOH | 16 | 1:1 | – d |
13 | 3a | EtOH | 4.5 | 1:1.5 | – |
14 | 3a | EtOH | 4.5 | 1.5:1 | 65 |
15 | 3a | EtOH | 4.5 | 2:1 | 66 |
Unless otherwise noted, all reactions were performed on a 0.33-mmol scale using the indicated ratio of 1a/2a, catalyst (20 mol%), solvent (1.5 mL), r.t., for the indicated time, followed by addition of the Wittig reagent (1.5 equiv) with reaction overnight.
Time for the domino reaction before the introduction of the Wittig reagent.
Isolated yield.
A mixture of 7 and 8 was obtained.