Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849, United States.
Org Lett. 2020 Nov 20;22(22):8967-8972. doi: 10.1021/acs.orglett.0c03366. Epub 2020 Oct 30.
The enantioselective - and -(borylmethyl)allylation of aldehydes via phosphoric acid catalysis is reported. Both ()- and ()-γ-borylmethyl allylboronate reagents were prepared via the Cu-catalyzed highly stereoselective protoboration of 1,3-dienylboronate. Chiral phosphoric acid-catalyzed aldehyde allylation with either the ()- or ()-allylboron reagent provided 1,2-- or 1,2--adducts in good yields with high enantioselectivities. The application to the synthesis of morinol D was accomplished.
通过磷酸催化，报告了醛的对映选择性 - 和 -(硼甲基)烯丙基化反应。通过 Cu 催化的 1,3-二烯基硼酸酯的高立体选择性原硼化反应，制备了 ()- 和 ()-γ-硼甲基烯丙基硼酸酯试剂。手性磷酸催化的醛与 ()-或 ()-烯丙基硼酸试剂的烯丙基化反应以高对映选择性和良好收率提供了 1,2--或 1,2--加合物。该方法应用于莫罗宁 D 的合成。
