N,N'-二氧化物-钪(III)配合物催化吲哚与亚烷基丙二酸酯的对映选择性傅克烷基化反应：β-咔啉的不对称合成

Enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates catalyzed by N,N'-dioxide-scandium(III) complexes: asymmetric synthesis of beta-carbolines.

作者信息

Liu Yanling, Shang Deju, Zhou Xin, Liu Xiaohua, Feng Xiaoming

机构信息

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China.

出版信息

Chemistry. 2009;15(9):2055-8. doi: 10.1002/chem.200802210.

DOI:10.1002/chem.200802210

PMID:19177478

Abstract

An efficient catalytic asymmetric Friedel-Crafts alkylation of indoles with alkylidene malonates has been developed by using a chiral N,N'-dioxide-Sc(OTf)(3) complex as the catalyst (see scheme). Some optically active intermediates containing the indole skeleton have been synthesized, such as indolepropionic acid, tryptamines, and beta-carbolines. The coordination between the scandium atom and the chiral N,N'-dioxide compound has been revealed by X-ray structure analysis.

摘要

通过使用手性N，N'-二氧化物-Sc(OTf)₃配合物作为催化剂，开发了一种高效的吲哚与亚烷基丙二酸酯的催化不对称傅克烷基化反应（见方案）。已经合成了一些含有吲哚骨架的光学活性中间体，如吲哚丙酸、色胺和β-咔啉。通过X射线结构分析揭示了钪原子与手性N，N'-二氧化物化合物之间的配位作用。