Regio- and Diastereoselective Synthesis of Cyclohexadienylborons via an Intermolecular Diels–Alder Reaction of Alkenyl MIDA Boronates with 2-Pyrones |
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Authors: | Wen-Xin Lv Zhan Li E Lin Ji-Lin Li Dong-Hang Tan Yuan-Hong Cai Qingjiang Li Honggen Wang |
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Institution: | School of Pharmaceutical Sciences, Sun Yat-sen University, 132 East Waihuan Road, College City, Guangzhou, 510006 P. R. China |
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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. |
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Keywords: | alkenyl boron bicyclolactones cyclohexadienylboron Diels–Alder reaction pyrones |
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