Remarkable Configurational Stability of Magnesiated Nitriles†
Dr. Graeme Barker
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)
Search for more papers by this authorMadeha R. Alshawish
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)
Search for more papers by this authorMelanie C. Skilbeck
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)
Search for more papers by this authorCorresponding Author
Prof. Iain Coldham
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)Search for more papers by this authorDr. Graeme Barker
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)
Search for more papers by this authorMadeha R. Alshawish
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)
Search for more papers by this authorMelanie C. Skilbeck
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)
Search for more papers by this authorCorresponding Author
Prof. Iain Coldham
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)
Department of Chemistry, University of Sheffield, Sheffield, S3 7HF (UK)Search for more papers by this authorWe would like to acknowledge The Leverhulme Trust, the Libyan Ministry of Higher Education, and the University of Sheffield for funding. We are grateful to Harry Adams for the single-crystal X-ray analysis.
Graphical 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).
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