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Cyclic Alkenenitriles:  Chemoselective Oxonitrile Cyclizations

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journal contribution
posted on 05.12.2002, 00:00 by Fraser F. Fleming, Lee A. Funk, Ramazan Altundas, Vaqar Sharief
Potassium tert-butoxide triggers the chemoselective cyclization between nitrile anions and remote, enolizable carbonyl groups, despite the acidity difference favoring enolate formation and addition to the nitrile group. Domino deprotonation, cyclization, and dehydration efficiently transform a diverse array of ω-oxonitriles into carbocyclic and heterocyclic five- and six-membered alkenenitriles in a single synthetic operation.