An efficient Bi/NH_4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

摘要

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.