通过樟脑基三环亚胺内酯与亚胺的非对映选择性曼尼希反应制备对映体纯的3-芳基-2,3-二氨基丙酸的便捷方法。

A convenient route to enantiopure 3-aryl-2,3-diaminopropanoic acids by diastereoselective Mannich reaction of camphor-based tricyclic iminolactone with imines.

作者信息

Zhang Huan-Huan, Hu Xiu-Qin, Wang Xiao, Luo Yong-Chun, Xu Peng-Fei

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China.

出版信息

J Org Chem. 2008 May 2;73(9):3634-7. doi: 10.1021/jo8001408. Epub 2008 Mar 26.

DOI:10.1021/jo8001408

PMID:18363371

Abstract

A novel and convenient route to the asymmetric synthesis of 2,3-diamino acids via Mannich reaction of iminolactones 1a and 1b with N-protected imines has been achieved in good yields (up to 95%) and high diastereoselectivity (dr: >99:1). Hydrolysis of the Mannich adducts under acidic conditions furnished the desired 3-aryl-2,3-diaminopropanoic acids in good yields (up to 85%) with excellent enantiomeric excesses (99% ee).

摘要

通过亚胺内酯1a和1b与N-保护的亚胺进行曼尼希反应，实现了一种新颖且便捷的不对称合成2,3-二氨基酸的方法，产率良好（高达95%）且非对映选择性高（dr：>99:1）。在酸性条件下水解曼尼希加合物，以良好的产率（高达85%）和优异的对映体过量（99% ee）得到所需的3-芳基-2,3-二氨基丙酸。