title: Remarkable configurational stability of magnesiated nitriles.
abstract: Quaternary stereocenters: Chiral α-magnesiated nitriles can be formed by deprotonation and are configurationally stable at low temperature, even for acyclic examples. These can be trapped with electrophiles to give enantiomerically enriched quaternary substituted products (see scheme; TMP = 2,2,6,6-tetramethylpiperidine).
authors.affiliation: Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, UK.
authors.forename: Graeme
authors.initials: G
authors.lastname: Barker
authors.forename: Madeha R
authors.initials: MR
authors.lastname: Alshawish
authors.forename: Melanie C
authors.initials: MC
authors.lastname: Skilbeck
authors.forename: Iain
authors.initials: I
authors.lastname: Coldham
mesh_terms: D000478:Alkylation; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry*; D011522:Protons; D013237:Stereoisomerism
chemical_list: D009570:Nitriles; D010880:Piperidines; D011522:Protons; C551336:2,2,6,6-tetramethylpiperidide; D008274:Magnesium
keywords: carbanions; configurational stability; nitriles; organomagnesium compounds; stereoselectivity