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.
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.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
1999年第12期1892-1896,共5页
Chemical Journal of Chinese Universities
基金
国家自然科学基金!(批准号:2977200 8)
国家杰出青年基金!(批准号:2972520 4)
中国科学院上海有机化学研究所金属有机开放实验室基
关键词
不对称合成
环丙胺化合物
5-羟基色胺
Asymmetric synthesis
Chiral cyclopropylamine
Asymmetric cyclopropanation
