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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

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Highly enantioselective metallation-substitution alpha to a chiral nitrile.

Sadhukhan Arghya A Hobbs Melanie C MC Meijer Anthony J H M AJHM Coldham Iain I

Chemical science 20161025 2

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). ...[more]

PMID: 28616143

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