Controllable Stereoselective Synthesis of (<i>Z</i>)<i>-</i> and (<i>E</i>)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction
作者:Yoshikazu Horino、Miki Sugata、Itaru Mutsuura、Keisuke Tomohara、Hitoshi Abe
DOI:10.1021/acs.orglett.7b02979
日期:2017.11.3
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 α,γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols
利用Pd催化3-(频哪醇硼基)烯丙基苯甲酸酯,醛和芳基锡烷的三组分反应,非对映选择性合成(Z)-和(E)-均烯丙基醇,为醛的烯丙基硼化提供了另一种方法用α,γ-二芳基取代的烯丙基硼酸酯。两组反应条件均允许获得具有良好至高烯烃立体控制的(Z)-或(E)-均烯丙基醇。本方法显示出良好的官能团相容性和通用性。还实现了有效的手性转移反应,以提供对映体富集的(Z)-和(E)-均烯丙基醇。