An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth-promoted Prins cyclization of imines with homoallyl alcohols.In the presence of 40 mol%BiCl_(3),a ...An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth-promoted Prins cyclization of imines with homoallyl alcohols.In the presence of 40 mol%BiCl_(3),a wide variety of imines react smoothly with homoallyl alcohols at room temperature to give the corresponding 4-chlorotetrahydropyran derivatives in good to excellent yields.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We are grateful for the financial support from the National Natural Science Foundation of China(No.21202154)Nanjing Institute of Technology Fund for Talents(No.YKJ201329)Nanjing Institute of Technology and the University of Science and Technology of China.
文摘An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth-promoted Prins cyclization of imines with homoallyl alcohols.In the presence of 40 mol%BiCl_(3),a wide variety of imines react smoothly with homoallyl alcohols at room temperature to give the corresponding 4-chlorotetrahydropyran derivatives in good to excellent yields.
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.
