Table 5. Enantioselective addition of phenylacetylene to N-benzylideneaniline in various solvents.
Entry | Solvent | Yield, % | ee % |
---|---|---|---|
1 | Toluene | 78 | 96 |
2 | Benzene | 74 | 97 |
3 | Heptane | 80 | 99 |
4 | Dichloromethane | 79 | 98 |
5 | Chloroform | 81 | 97 |
6 | 1,2-Dichloroethane | 71 | 99.5 |
7 | Carbon tetrachloride | 25 | 99.4 |
8 | 1,4-Dioxane | 82 | 98 |
9 | Tetrahydrofuran | 65 | 96 |
10 | Ethyl acetate | 53 | 98 |
11 | Acetone | 80 | 99 |
12 | N,N-dimethylformamide | 80 | 97 |
13 | Acetonitrile | 82 | 99 |
14 | Methanol | 85 | 88 |
15 | Triethylamine | 48 | 97 |
16 | Water | 71 | 84 |