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. Author manuscript; available in PMC: 2012 Feb 8.
Published in final edited form as: Chemistry. 2011 Jun 3;17(29):8000–8004. doi: 10.1002/chem.201101049

Table 1.

Allylation reactions of 3,3-disubstitued allylzinc species with various aldehydes.[a]

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
[a]

Hex=hexyl.

[b]

Determined after purification by column chromatography on alumina.

[c]

Determined by analysis of the crude product by 1H NMR spectroscopy and gas chromatography.

[d]

For aliphatic aldehydes, the allylation reaction proceeds at −40°C and the increased temperature can explain the lower diastereoselectivity.