光学活性Ugi胺的简便合成方法

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

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.