1. Highly enantioselective metallation–substitution alpha to a chiral nitrile
- Author
-
Iain Coldham, Anthony J. H. M. Meijer, Arghya Sadhukhan, and Melanie C. Hobbs
- Subjects
Nitrile ,010405 organic chemistry ,Chemistry ,organic chemicals ,Enantioselective synthesis ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,0104 chemical sciences ,3. Good health ,chemistry.chemical_compound ,Deprotonation ,Electrophile ,polycyclic compounds ,Organic chemistry ,heterocyclic compounds - Abstract
We report the deprotonation of a chiral nitrile and reaction of the resulting chiral organometallic species with a variety of electrophiles to give highly enantiomerically enriched 2-substituted nitrile products. The nitrile was treated with TMPMgCl and the resulting anion, an asymmetric alpha cyano Grignard species, was found to be configurationally stable at low temperature for a short time (half-life several minutes at −104 °C).
- Published
- 2017