【摘要】 利用手性双唑啉与三氟甲磺酸亚铜催化 2 -甲氧基苯乙烯与重氮乙酸二环己基甲酯的不对称环丙烷化反应合成了手性环丙烷羧酸酯 ,用氢氧化钠对其进行选择性水解得到全反式环丙烷羧酸 ,其 ee值经 GC测定为 88% .进一步经过 Curtius重排、烷基化等反应及重结晶等步骤合成了光学纯的具有生理活性的环丙胺化合物 1a和 1b.更多还原

【Abstract】 The synthesis of the potent 5 HT receptor agonist( 1R,2S ) (-) 2 (2 hydroxyphenyl) N,N propylcyclopropamine was described in this paper. Asymmetric cyclopropanation of 2 methoxystyrene with(dicyclohexyl)methyl diazoacetate in the presence of 1%(molar fraction) copper(Ⅰ) triflate and bis(oxazoline) ligand gave chiral cyclopropane 1 carboxylate. After selecting alkaline hydrolysis, trans cyclopropane 1 carboxylic acid was obtained. The subsequent Curtius rearrangement and hydrolysis in dilute hydrochloric acid were accomplished to yield the( 1R,2S) (-) 2 (2 methoxyphenyl)cyclopropylamine. N,N Dialkylation with n propyliodide and demethylation by 48% aq. HBr provided the desired optically pure( 1R,2S ) (-) 2 (2 hydroxyphenyl) N,N dipropylcyclopropylamine.更多还原