The first enantioenriched metalated nitrile possessing macroscopic configurational stability

被引：33

作者：

Carlier, Paul R. ^{[1
]}

Zhang, Yiqun ^{[1
]}

机构：

[1] Virginia Tech, Dept Chem, Blacksburg, VA 24061 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 07期

关键词：

D O I：

10.1021/ol070149g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Magnesium-bromine exchange on enantiopure cyclopropyl bromonitrile 5 at -100 degrees C for 1 min followed by a D2O quench gives the deuterionitrile in 81% ee (retention); additional trapping experiments establish t(1/2)(rac) = 11.4 h at -100 degrees C. These experiments provide the first glimpse into the stereochemical aspects of Mg-Br exchange. The intermediate formed is the first metalated nitrile demonstrated to possess macroscopic configurational stability.

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页码：1319 / 1322

页数：4

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