Kirchhoff JH, Bräse S, Enders D
RWTH Aachen, Institut für Organische Chemie, Professor-Pirlet-Strasse 1, 52074 Aachen, Germany.
J Comb Chem. 2001 Jan 8;3(1):71-77. doi: 10.1021/cc000062l.
A novel hydrazine linker resin for solid-phase organic synthesis has been developed. Starting from Merrifield resin, the new N-butyl-N-methylpolystyrene-hydrazine linker is prepared in three steps. Polymer-supported hydrazones, readily prepared from aldehydes and the hydrazine resin, react with alkyl- and arylorganolithium reagents under 1,2-addition to the C-N double bond to afford the corresponding hydrazines. Release from solid support was achieved by reductive N-N bond cleavage using the borane-tetrahydrofuran complex. The resulting alpha-branched primary amines were protected as their amides or carbamates, respectively, and, after purification, were obtained in good overall yields and in high purity (12 examples).
一种用于固相有机合成的新型肼连接树脂已被开发出来。从Merrifield树脂开始，通过三步制备新的N-丁基-N-甲基聚苯乙烯-肼连接体。聚合物负载的腙可由醛和肼树脂轻松制备，在1,2-加成到C-N双键的条件下与烷基和芳基有机锂试剂反应，得到相应的肼。通过使用硼烷-四氢呋喃络合物进行还原N-N键裂解实现从固相载体上释放。所得的α-支链伯胺分别被保护为它们的酰胺或氨基甲酸酯，经过纯化后，以良好的总收率和高纯度得到（12个实例）。
