Table 1. Solvent, Temperature, and Substituents Effects on the Uncatalyzed Reaction between 1 and 2a.
conversion (%) |
||||||
---|---|---|---|---|---|---|
entry | substrate | T (°C) | solvent | 1 h | 2 h | 4 h |
1 | 1a | rt | toluene | 4 | 6 | 10 |
2 | 1a | rt | DCM | 2 | 4 | 7 |
3 | 1a | rt | THF | 5 | 6 | 9 |
4 | 1a | rt | iPrOH | 7 | 11 | 20 |
5 | 1a | rt | tBuOAc | 5 | 8 | 11 |
6 | 1a | rt | anisole | 3 | 4 | 7 |
7 | 1a | rt | DMC | 2 | 3 | 6 |
8 | 1c | rt | toluene | 4 | 6 | 8 |
9 | 1f | rt | toluene | 5 | 9 | 14 |
10 | 1h | rt | toluene | 2 | 6 | 10 |
11 | 1i | rt | DCM | 1 | 2 | 4 |
12 | 1j | rt | DCM | 2 | 3 | 4 |
13 | 1l | rt | toluene | 27 | 48 | 76 |
14 | 1l | 0 | toluene | 3 | 6 | 12 |
15 | 1l | –10 | toluene | 2 | 3 | 5 |
16 | 1n | rt | toluene | 11 | 21 | 32 |
17 | 1o | rt | toluene | 2 | 3 | 5 |
All reactions were carried out with 20 mol % excess of aldehyde, 0.5 M concentration, and the conversion was monitored by HPLC. The reported data are a selection of a more extended screening (see Supporting Information).