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The first enantioenriched metalated nitrile possessing macroscopic configurational stability.

作者信息

Carlier Paul R, Zhang Yiqun

机构信息

Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA.

出版信息

Org Lett. 2007 Mar 29;9(7):1319-22. doi: 10.1021/ol070149g. Epub 2007 Mar 10.

DOI:10.1021/ol070149g
PMID:17348666
Abstract

[structure: see text]. 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.

摘要

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