在鋅存在下，烯丙基鹵代物親核加成到醛酮上得到高烯丙醇的反應。此反應可以在水中反應，也可不加溶劑固體直接混合反應。此反應和Barbier反應類似。
反應實例
1-Decen-4-ol (3). A mixture of heptaldehyde 1 (119.5 mg, 1.05 mmol), sat aq NH4Cl (1 mL), reverse phase resin (C18, 200 mg), allyl bromide (0.1 mL) and Zn dust (78 mg, 1.2 mmol) was stirred overnight at 20 ℃ open to air. Filtration, washing with Et2O and solvent evaporation afforded 160 mg of 3 (98%).
【W(wǎng)ilson SR, J Org Chem, 1989, 54, 3087】
1-Allylcyclohexanol (5). 4 (500 mg, 5.1 mmol), 2 (3.09 g, 25.5 mmol), Zn powder (5 g) and NH4Cl (2 g) were ground in an agate mortar with pestle and the mixture was kept for 2 h at 20 C. Workup and evaporation gave 642 mg of 5 (90%).
【Toda F, J Org Chem, 1991, 56, 4333】
相關文獻
1 Luche JL J Org Chem 1985 50 910
2 Luche JL Tet Lett 1985 26 1449
3 Luche JL J Organomet Chem 1987 322 177
4 Wilson SR J Org Chem 1989 54 3087
5 Toda F J Org Chem 1991 56 4333
6 Wang Z ARKIVOC 2004 ix 52
7 Ley SV Angew Chem Int 2005 44 5433
8 Lee HW Bull Kor Chem Soc 2008 29 1663
編譯自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 296.
