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  • Title: Metalated nitriles: electrophile-dependent alkylations.
    Author: Fleming FF, Zhang Z, Wei G, Steward OW.
    Journal: Org Lett; 2005 Feb 03; 7(3):447-9. PubMed ID: 15673261.
    Abstract:
    [reaction: see text] Sequential carbonyl addition-conjugate addition to oxonitriles generates a C-magnesiated nitrile exhibiting electrophile-dependent alkylation stereoselectivities. Alkylations with alkyl halides, sulfonates, and ketones proceed with retention of stereochemistry, whereas aldehyde and acyl cyanide acylations proceed with inversion of stereochemistry. BuLi-initiated conversion of the C-magnesiated nitrile to the corresponding N-lithiated nitrile reverses the alkylation stereoselectivity, providing a facile route to diastereomeric nitriles that vary at a single, quaternary stereocenter.
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