An efficient method was developed for the conjugate addition of water to various a,β-unsaturated ketones by using bismuth(Ⅲ)chlo ride as a catalyst.The reactions proceeded smoothly in the presence of a catalytic amo...An efficient method was developed for the conjugate addition of water to various a,β-unsaturated ketones by using bismuth(Ⅲ)chlo ride as a catalyst.The reactions proceeded smoothly in the presence of a catalytic amount of BiCl3(20 mol%)in aqueous media to furnish a variety of synthetically usefulβ-hydroxyl ketones in moderate to good yields.Apart from water molecule,various alcohols could also be employed as nucleophiles to react withα,β-unsaturated ketones,leading toβ-alkoxyl ketones in modest to high yields.In addition,the mild reaction conditions also entailed the conjugate addition reactions to proceed with the tolerance to a range of functional groups.展开更多
An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed.The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford th...An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed.The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities(>99:1 syn:anti).Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.展开更多
基金financial support from Nanjing Tech University(Start-up Grant No.39837118)Yancheng Teachers University,and Nanjing Forestry University。
文摘An efficient method was developed for the conjugate addition of water to various a,β-unsaturated ketones by using bismuth(Ⅲ)chlo ride as a catalyst.The reactions proceeded smoothly in the presence of a catalytic amount of BiCl3(20 mol%)in aqueous media to furnish a variety of synthetically usefulβ-hydroxyl ketones in moderate to good yields.Apart from water molecule,various alcohols could also be employed as nucleophiles to react withα,β-unsaturated ketones,leading toβ-alkoxyl ketones in modest to high yields.In addition,the mild reaction conditions also entailed the conjugate addition reactions to proceed with the tolerance to a range of functional groups.
基金financial support from Nanjing Tech University(Start-up Grant No.39837118)Yancheng Teachers UniversityNanjing Forestry University。
文摘An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed.The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities(>99:1 syn:anti).Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.
