STEREOSELECTIVE REDUCTION OF SOME INDOLES WITH TRIETHYLSILANE-TRIFLUOROACETIC ACID

被引：70

作者：

LANZILOTTI, AE ^{[1
]}

LITTELL, R ^{[1
]}

FANSHAWE, WJ ^{[1
]}

MCKENZIE, TC ^{[1
]}

LOVELL, FM ^{[1
]}

机构：

[1] AMER CYANAMID CO,LEDERLE LABS,DIV MED RES,PEARL RIVER,NY 10965

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 26期

关键词：

D O I：

10.1021/jo00394a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The completely stereoselective reduction of indoles to cis-indolines by triethylsilane-trifluoroacetic acid is demonstrated. A rationalization of this stereoselectivity is offered. The precursor indoles were prepared by the Fisher indole condensation with levulinic acid (7). 3, 4-Dimethoxyhydrazine (6a) gave only the 5, 6-dimethoxyindole 8a while 3, 4-dichlorohydrazine (6d) gave a 1:1 mixture of the isomeric chloroindoles 8d and 8e which were separated by preparative liquid chromatography. © 1979, American Chemical Society. All rights reserved.

引用

页码：4809 / 4813

页数：5

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