Table 1.
Starting material | R1 | R2 | R3 | Product | Yield [%][b] | d.r.[c] | |
---|---|---|---|---|---|---|---|
1 | 3a | Hex | Et | p-BrH4C6 | 7a | 71 | 97:3 |
2 | 3b | Et | Hex | p-BrH4C6 | 7b | 55 | 90:10 |
3 | 3c | Hex | Bu | p-BrH4C6 | 7c | 60 | 98:2 |
4 | 3d | Bu | Et | p-BrH4C6 | 7d | 70 | 92:8 |
5 | 3e | Me | Et | p-BrH4C6 | 7e | 52 | 90:10 |
6 | 3a | Hex | Et | p-MeH4C6 | 7 f | 60 | 98:2 |
7 | 3d | Bu | Et | H5C6 | 7g | 70 | 98:2 |
8 | 3d | Bu | Et | p-OAcH4C6 | 7h | 63 | 88:12 |
9 | 3d | Bu | Et | p-MeO2CH4C6 | 7i | 65 | 88:12 |
10[d] | 3b | Hex | Et | nBu | 7j | 70 | 96:4 |
11[d] | 3a | Et | Hex | nBu | 7k | 66 | 91:9 |
12[d] | 3d | Bu | Et | Ph(CH2)2 | 7l | 62 | 83:17 |
13[d] | 3d | Bu | Et | iPr | 7m | 41 | 80:20 |
Hex=hexyl.
Determined after purification by column chromatography on alumina.
Determined by analysis of the crude product by 1H NMR spectroscopy and gas chromatography.
For aliphatic aldehydes, the allylation reaction proceeds at −40°C and the increased temperature can explain the lower diastereoselectivity.