Table 1.
entry | Lewis acid | equiv | temp (°C) | solvent | dr |
---|---|---|---|---|---|
1 | MgBr2·OEt2 | 2.0 | −20 | CH2Cl2 | 4 : 1 |
2 | MgBr2·OEt2 | 2.0 | −78 to −20 | CH2Cl2 | 4.5 : 1 |
3 | BF3·OEt2 | 1.1 | −78 | CH2Cl2 | 5 : 1 |
4 | TiCl3(OiPr) | 1.0 | −78 | PhCH3 | 5 : 1 |
5 | TiCl2(OiPr)2 | 1.0 | −78 | PhCH3 | 32 : 1a |
6 | TiCl2(OiPr)2 | 2.0 | −78 | PhCH3 | 37 : 1b |
7 | TiCl2(OiPr)2 | 2.5 | −78 | PhCH3 | 41 : 1c |
40% of 16 recovered.
10% of 16 recovered.
95% of 17 isolated.