Graduate School of Science and Engineering, University of Toyama , 3190 Gofuku, Toyama 930-8555, Japan.
Department of Hospital Pharmacy, University of Toyama , 2630 Sugitani, Toyama 930-0194, Japan.
Org Lett. 2017 Nov 3;19(21):5968-5971. doi: 10.1021/acs.orglett.7b02979.
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 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.
使用 Pd 催化的 3-(频哪醇硼酸酯基)烯丙基苯甲酸酯、醛和芳基锡烷的三组分反应，发展了（Z）-和（E）-高烯丙醇的非对映选择性合成，为使用α，γ-二芳基取代的烯丙基硼酸酯对醛进行烯丙基硼化提供了一种替代方法。这两种反应条件都能以良好到高的烯烃立体选择性得到（Z）-或（E）-高烯丙醇。本方法表现出良好的官能团相容性和通用性。也实现了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。
