A Novel Hydrazine Linker Resin and Its Application for the Solid-Phase Synthesis of α-Branched Primary Amines

摘要: A novel hydrazine linker resin for solid-phase organic synthesis has been developed. Starting from Merrifield resin, the new N-butyl-N-methylpolystyrene-hydrazine is prepared in three steps. Polymer-supported hydrazones, readily aldehydes and react with alkyl- arylorganolithium reagents under 1,2-addition to C−N double bond afford corresponding hydrazines. Release solid support was achieved by reductive N−N cleavage using borane-tetrahydrofuran complex. The resulting α-branched primary amines were protected as their amides or carbamates, respectively, and, after purification, obtained good overall yields high purity (12 examples).