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4,7-二氢吲哚与α,β-不饱和醛的有机催化对映选择性傅克烷基化反应:一种简便合成2-取代吲哚的方法

Organocatalytic enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with alpha,beta-unsaturated aldehydes: an easy access to 2-substituted indoles.

作者信息

Hong Liang, Liu Chunxia, Sun Wangsheng, Wang Lei, Wong Kwokyin, Wang Rui

机构信息

State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, China.

出版信息

Org Lett. 2009 May 21;11(10):2177-80. doi: 10.1021/ol900461v.

Abstract

An enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles and alpha,beta-unsaturated aldehydes has been developed. The process is promoted by diphenylprolinol ether to afford 2-substituted 4,7-dihydroindoles in high yields and enantioselectivities. After a subsequent oxidation of the products, the optically active 2-substituted indoles could be obtained smoothly in high yields without any loss of enantioselectivity.

摘要

已开发出4,7-二氢吲哚与α,β-不饱和醛的对映选择性傅克烷基化反应。该反应由二苯基脯氨醇醚促进,以高收率和对映选择性得到2-取代的4,7-二氢吲哚。在对产物进行后续氧化后,可以高收率顺利得到光学活性的2-取代吲哚,且对映选择性没有任何损失。

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