Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction
Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction
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DOI：
10.1021/acs.orglett.7b02979
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发表时间：
2017-11-03
期刊：
影响因子：
5.2
通讯作者：
Abe, Hitoshi
中科院分区：
文献类型：
--
作者：
Horino, Yoshikazu;Sugata, Mild;Abe, Hitoshi
以3-（频哪醇基）苯甲酸烯丙酯、醛和芳基锡烷为原料，在钯催化下，非对映选择性合成了（Z）-和（E）-高烯丙醇，为α，γ-二芳基取代的烯丙基硼酸酯与醛的烯丙基硼化反应提供了一种新的方法。两组反应条件都能够获得具有良好到高度烯烃立体控制的（Z）-或（E）-高烯丙醇。该方法具有良好的官能团兼容性和通用性。通过高效的手性转移反应得到了对映体富集的（Z）-和（E）-高烯丙醇。
Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using alpha,gamma-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.