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Regio- and Diastereoselective Synthesis of Cyclohexadienylborons via an Intermolecular Diels–Alder Reaction of Alkenyl MIDA Boronates with 2-Pyrones
Authors:Wen-Xin Lv  Zhan Li  E Lin  Ji-Lin Li  Dong-Hang Tan  Yuan-Hong Cai  Qingjiang Li  Honggen Wang
Institution:School of Pharmaceutical Sciences, Sun Yat-sen University, 132 East Waihuan Road, College City, Guangzhou, 510006 P. R. China
Abstract:An efficient synthesis of highly functionalized cyclohexadienylborons via an inverse electron-demand Diels–Alder reaction/CO2 extrusion of alkenyl MIDA boronates with 2-pyrones is outlined. By controlling the reaction temperature, the corresponding C(sp3)-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.
Keywords:alkenyl boron  bicyclolactones  cyclohexadienylboron  Diels–Alder reaction  pyrones
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