Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans
Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans
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DOI：
10.1021/ol0346180
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发表时间：
2003-07-10
期刊：
影响因子：
5.2
通讯作者：
Willis, CL
中科院分区：
文献类型：
--
作者：
Barry, CSJ;Crosby, SR;Willis, CL
在TFA存在下，高烯丙醇与醛反应生成4-羟基-2，3，6-三取代四氢吡喃，生成三个新的立体中心；一锅法。通过改变醛组分，在C-2上安装了各种官能化的侧链。将该方法应用于~gt；99%ee的四氢吡喃的对映选择性合成。
graphicReaction of homoallylic alcohols with aldehydes in the presence of TFA gives, after hydrolysis of the ester, 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans with the creation of three new stereocenters; in a single-pot process. By varying the aldehyde component, a variety of functionalized side chains are installed at C-2. The utility of this approach is extended to the enantioselective synthesis of tetrahydropyrans with >99% ee.