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Deprotonating γ- and δ-hydroxynitriles with i-PrMgCl allows highly diastereoselective alkylations controlled by the asymmetry of the remote carbinol stereocenter. Mechanistic experiments are consistent with γ-hydroxynitriles alkylating via a chelated magnesiated nitrile whereas δ-hydroxynitriles favor alkylation from acyclic magnesiated nitriles. Collectively these alkylations; are the first electrophile-dependent...
Nitrile and enolate anions exhibit divergent intramolecular cyclization stereoselectivities. Enolates cyclize to cis-decalones, whereas nitrile anions are predisposed to pyramidalize, cyclizing instead through a less-congested conformation to trans-decalins. Conjugation of nitrile anions with adjacent sp 2 centers prevents pyramidalization, and redirects cyclization through a planar-delocalized...
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