(-)-Sparteine辅助的邻位锂化反应对映选择性合成具有平面手性的非对称二茂铁胺  

Enantioselective Synthesis of Unsymmetrical Ferrocenenylamides with Planar Chirality by(-)-Sparteine Mediated Directed ortho-Lithiation

作　　者：周智明[1] 袁浩[1] Snieckus,Victor 

机构地区：[1]北京理工大学化工与环境学院,北京100081 [2]Department of Chemistry, Queen's University, Kingston ON KL7 3N6, Canada

出　　处：《有机化学》2010年第11期1754-1758,共5页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20572009)资助项目

摘　　要：以非对称的N-乙基-N-异丙基-二茂铁酰胺为底物,利用(-)-sparteine辅助的邻位锂化反应制备具有平面手性的二茂铁衍生物,得到了很高的产率和对映选择性.并测定了1-(N-乙基-N-异丙基)酰胺-2-碘-二茂铁(10a)的晶体结构.研究发现,非对称的二茂铁底物有利于强化底物的手性环境,进而提高反应的对映选择性.The unsymmetrical ferrocene substrate,{[N-ethyl-N-（1-methylethyl）-amino]-carbonyl}-ferro-cene,was used in（-）-sparteine mediated directed ortho-lithiation to prepare the planer chiral ferrocene ligands.High yields and enatioselectivities were obtained.Increased enatioinductions were observed in re-search work by introducing the unsymmetrical N-ethyl-N-（1-methylethyl）-carboxamide group.Moreover,crystal structure of the compound 1-{[N-ethyl-N-（1-methylethyl）-amino]carbonyl}-2-iodo-ferrocene（10a）,was detected by X-ray single-crystal diffraction.The absolute configuration was determined as R for the planar chirality.

关 键 词：(-)-Sparteine 邻位锂化反应 非对称二茂铁胺 平面手性二茂铁 晶体结构 

分 类 号：O621.34[理学—有机化学]