光学活性Ugi胺的简便合成方法  

Convenient Preparation of (S)-and (R)-Ugi’s Amines

作　　者：宋定国[1] 年三飞 陈佳琛 罗文俊[1] 王泽 凌飞[1] 钟为慧[1] SONG Dingguo;NIAN Sanfei;CHEN Jiachen;LUO Wenjun;WANG Ze;LING Fei;ZHONG Weihui(Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals,College of Pharmaceutical Sciences,Zhejiang University of Technology,Hangzhou 310014)

机构地区：[1]浙江工业大学药学院,长三角绿色制药协同创新中心,浙江杭州310014

出　　处：《中国医药工业杂志》2020年第2期189-192,共4页Chinese Journal of Pharmaceuticals

摘　　要：本试验报道了一种可公斤级制备光学活性Ugi胺的方法。以课题组自制的手性二茂铁PNN配体(L1或L2)与贵金属Ir组成的复合物为催化剂CAT-1或CAT-2,叔丁醇锂为碱,异丙醇为溶剂,促进乙酰二茂铁的不对称氢化,分别以高收率、高立体选择性得到(S)-或(R)-1-二茂铁基乙醇;再经过简单的酯化、二甲胺取代,即可公斤级制备(S)-和(R)-Ugi胺,ee值高达99.2%,具有工业化应用前景。A method for the preparation of(S)-and(R)-Ugi’s amines in kilogram-scale was reported herein. A complex of a chiral ferrocene PNN ligand(L1 or L2) developed by our group and a noble metal Ir was used as a catalyst(CAT-1 or CAT-2), lithium t-butoxide was used as a base, and isopropanol was used as a solvent to asymmetrically hydrogenate acetylferrocene.(S)-or(R)-1-ferrocenylethanol was obtained in high yield and high stereoselectivity, respectively.(S)-and(R)-Ugi’s amines could be readily prepared with up to 99.2% ee value through esterification of(S)-or(R)-1-ferrocenylethanol, followed by esterification and the substitution of dimethylamine, which has industrial application prospects.

关 键 词：Ugi胺 手性二茂铁PNN配体 不对称氢化 乙酰二茂铁 公斤级 

分 类 号：O626[理学—有机化学] TQ426.94[理学—化学]