Metalation-Substitution of an α-Oxygenated Chrial Nitrile

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

doi:10.1016/j.crci.2016.11.006

Metalation-Substitution of an α-Oxygenated Chrial Nitrile

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

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

99 Downloads (Pure)

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.

Original language	English
Pages (from-to)	601-608
Number of pages	8
Journal	Comptes Rendus Chimie
Volume	20
Issue number	6
Early online date	21 Dec 2016
DOIs	https://doi.org/10.1016/j.crci.2016.11.006
Publication status	Published - Jun 2017

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title = "Metalation-Substitution of an α-Oxygenated Chrial Nitrile",

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.",

author = "Madeha Alshawish and Graeme Barker and Measom, \{Nicholas D.\} and Iain Coldham",

year = "2017",

month = jun,

doi = "10.1016/j.crci.2016.11.006",

language = "English",

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pages = "601--608",

journal = "Comptes Rendus Chimie",

issn = "1631-0748",

publisher = "Academie des sciences",

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T1 - Metalation-Substitution of an α-Oxygenated Chrial Nitrile

AU - Alshawish, Madeha

AU - Barker, Graeme

AU - Measom, Nicholas D.

AU - Coldham, Iain

PY - 2017/6

Y1 - 2017/6

N2 - 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.

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.

U2 - 10.1016/j.crci.2016.11.006

DO - 10.1016/j.crci.2016.11.006

M3 - Article

SN - 1631-0748

VL - 20

SP - 601

EP - 608

JO - Comptes Rendus Chimie

JF - Comptes Rendus Chimie

IS - 6

ER -

Metalation-Substitution of an α-Oxygenated Chrial Nitrile

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