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A rare 5-exo-dig SNi′ cyclization with magnesiated and lithiated nitriles affords a cis-fused hydrindane bearing an exocyclic allene. The cyclization of the dilithiated nitrile pits a stereoelectronic preference for a trans-hydrindane against a cyclization through a less strained transition structure to the corresponding cis-hydrindane. Computational modeling suggests that the dilithiated nitrile...
Double deprotonation of β-hydroxynitriles with MeMgCl (2.1 equiv.) generates a dianion that ejects MgO to provide the corresponding α,β-unsaturated nitriles. Structurally diverse β-hydroxynitriles readily eliminate MgO providing an expedient route to highly substituted α,β-unsaturated nitriles.
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