Metalation-Substitution of an α-Oxygenated Chrial Nitrile

Madeha Alshawish, Graeme Barker, Nicholas D. Measom, Iain Coldham

Research output: Contribution to journalArticle

Abstract

Deprotonation of a chiral alpha-oxygenated nitrile with the base 2,2,6,6-tetramethylpiperidylmagnesiumchloride, TMPMgCl, gives rise to a chiral magnesiated nitrile, and thisanion has sufficient configurational stability at low temperature to allow the formation ofhighly enantiomerically enriched substituted nitrile products after electrophilic quench.
LanguageEnglish
Pages601-608
Number of pages8
JournalComptes Rendus Chimie
Volume20
Issue number6
Early online date21 Dec 2016
DOIs
Publication statusPublished - Jun 2017

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Alshawish, Madeha ; Barker, Graeme ; Measom, Nicholas D. ; Coldham, Iain. / Metalation-Substitution of an α-Oxygenated Chrial Nitrile. In: Comptes Rendus Chimie. 2017 ; Vol. 20, No. 6. pp. 601-608.
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Metalation-Substitution of an α-Oxygenated Chrial Nitrile. / Alshawish, Madeha; Barker, Graeme; Measom, Nicholas D.; Coldham, Iain.

In: Comptes Rendus Chimie, Vol. 20, No. 6, 06.2017, p. 601-608.

Research output: Contribution to journalArticle

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AB - Deprotonation of a chiral alpha-oxygenated nitrile with the base 2,2,6,6-tetramethylpiperidylmagnesiumchloride, TMPMgCl, gives rise to a chiral magnesiated nitrile, and thisanion has sufficient configurational stability at low temperature to allow the formation ofhighly enantiomerically enriched substituted nitrile products after electrophilic quench.

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