School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, Jiangsu, China.
J Org Chem. 2011 Mar 18;76(6):1831-7. doi: 10.1021/jo102516a. Epub 2011 Feb 17.
A simple, efficient, and general α-prenylation approach for the synthesis of a variety of α-prenylated alcohols has been successfully developed. A wide range of α-prenylated alcohol derivatives could be obtained in good yields by highly α-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120 °C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product. The method provides a convenient route for the direct α-prenylation of carbonyl compounds in a highly α-regioselective manner using a cheap and convenient mediator. Two possible pathways are proposed to account for the formation of these synthetically difficult-to-obtain molecules.
已成功开发出一种简单、高效、通用的α-烯丙基化方法，用于合成各种α-烯丙基醇。通过在 HMPA 中用烯丙基溴在 120°C 下高度α-区域选择性地对各种醛和酮进行锌介导的烯丙基化，可高收率得到广泛的α-烯丙基醇衍生物。通过简单改变反应溶剂和温度，该方法可以实现高度显著的相反区域控制，得到预期的区域化学产物。该方法为使用廉价方便的试剂以高度α-区域选择性方式直接对羰基化合物进行α-烯丙基化提供了一种方便的途径。提出了两种可能的途径来解释这些难以合成的分子的形成。
