Determination of the absolute configuration of a secondary alcohol by NMR spectroscopy using difluorodinitrobenzene

被引：10

作者：

Harada, K ^{[1
]}

Shimizu, Y ^{[1
]}

Kawakami, A ^{[1
]}

Fujii, K ^{[1
]}

机构：

[1] Meijo Univ, Fac Pharm, Tempaku Ku, Nagoya, Aichi 4688503, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(99)01926-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile method was developed to determine the absolute configuration of a secondary alcohol using the characteristic functions of 1,5-difluoro-2,4-dinitrobenzene (FFDNB). In this method, a secondary alcohol reacted first with FFDNB under mild basic conditions, and 1-phenylethylamine was then introduced into the secondary alcohol-FDNB derivative for the recognition by the NMR spectral method. Because the conformations of the resulting derivatives are rigidly fixed by the dinitrobenzene plane, the absolute configuration at the asymmetric carbon of the secondary alcohol tested can be definitively deduced using the NMR anisotropic effect. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：9081 / 9084

页数：4

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