(Z)-Alpha-bromo-1-alkenylboronate esters readily react with (1,3-dioxan-2ylethyl) magnesium bromide in ether at low temperature. After stirring at room temperature, the reaction provides (E)-1-(1,3-dioxan-2elethyl) l-1 alkenyl boronate esters. It is then reacted with phenyllithium followed by treatment with iodine in tetrahydrofuran at low temperature. After workup, the corresponding (Z)-trisubstituted alkenes containing phenyl and and 1,3_dioxan-2ylethyl) moieties. The products are obtained in 72%-80% yields. They are purified by column chromatography over alumina and the structures are confirmed by NMR spectral data.

Highly daistereoselective synthesis of (Z)-trisubstituted alkenes containing phenyl and (1,3-dioxan-2ylethul) moieties via organoboranes

2019 Spring National Meeting

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