在锌存在下,烯丙基卤代物亲核加成到醛酮上得到高烯丙醇的。此反应可以在水中反应,也可不加溶剂固体直接混合反应。此反应和Barbier反应类似。
反应实例
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%).
【Wilson 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】
相关文献
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
编译自:Organic Syntheses Based On , 3RdEd, A. Hassner, Page 296.
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