Luche锌烯丙化反应
2020-10-28 01:12:51   来源:

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反应。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 Chem1989, 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 Chem1991, 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 Name Reactions, 3RdEd, A. Hassner, Page 296.

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