Wiley-VCH Verlag, ChemInform, 16(39), 2008
Taylor and Francis Group, Synthetic Communications, 22(37), p. 3923-3931
DOI: 10.1080/00397910701572456
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A synthetic pathway that produces alkyl α,-cyanodiolefins in quantitative yield is described, applying chemistry that is based on simple α-alkylation of alkyl nitriles. Three amide bases, lithium 2,2,6,6-tetramethylpiperidide, lithium diisopropylamide, and sodium amide, are used to create the α-carbanions that undergo substitution with various alkylating agents. Optimization leads to essentially quantitative conversions for every substrate/example reported herein, which will prove useful in many synthetic schemes.