二胺
对称化
化学
对映选择合成
诺博南
联氨(抗抑郁剂)
有机化学
对映体过量
对映体
降冰片烯
配体(生物化学)
催化作用
单体
生物化学
受体
聚合物
色谱法
作者
Cihangir Tanyeli,Salih Özçubukçu
标识
DOI:10.1016/s0957-4166(03)00161-7
摘要
The asymmetric synthesis of trans-2,3-bis(aminomethyl)norbornane was performed starting with endo-2,3-norbornene dicarboxylate anhydride. Desymmetrization of meso-anhydride 1 and following selective epimerization gave the trans-monoester (+)-3 with a high enantiomeric excess (98% e.e.). LiAlH4 reduction of the trans-monoester to the 1,4-diol, which was then treated with phthalimide under Mitsunobu conditions and, following a Gabriel type amine synthesis with hydrazine hydrate, yielded a saturated and unsaturated diamine mixture. Hydrogenation of mixture finally afforded saturated diamine (+)-8 with a yield of 37%.
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