School of Pharmaceutical Sciences, Sun Yat-sen University, 132 East Waihuan Road, College City, Guangzhou, 510006, P. R. China.
Chemistry. 2019 Mar 15;25(16):4058-4061. doi: 10.1002/chem.201900011. Epub 2019 Feb 22.
An efficient synthesis of highly functionalized cyclohexadienylborons via an inverse electron-demand Diels-Alder reaction/CO extrusion of alkenyl MIDA boronates with 2-pyrones is outlined. By controlling the reaction temperature, the corresponding C(sp )-rich bicyclolactones could also be readily formed. The exo-selective reactions feature good functional-group tolerance, broad substrate scope, and excellent regio- and diastereoselectivity. Oxidation of the cyclohexadienylborons in a one-pot procedure led to the construction of aromatic boronates bearing valuable functional groups. Synthetic transformations of the C-B bond were demonstrated.
通过烯基 MIDA 硼酸酯与 2-吡喃酮的逆电子需求 Diels-Alder 反应/CO 挤出，高效合成了高度官能化的环己二烯基硼。通过控制反应温度，也可以很容易地形成相应的 C(sp )-富双环内酯。反式选择性反应具有良好的官能团耐受性、广泛的底物范围和优异的区域和立体选择性。在一锅法中，对环己二烯基硼进行氧化，构建了具有有价值官能团的芳基硼酸酯。还展示了 C-B 键的合成转化。
