Highly enantioselective metallation-substitution alpha to a chiral nitrile.

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).

SUBMITTER: Sadhukhan A 

PROVIDER: S-EPMC5460602 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature