Cyanide is a useful one-carbon nucleophile that readily participates in conjugate addition reactions with α,β-unsaturated ketones and esters to form β-cyano carbonyl compounds. However, cyanide does not readily react with α,β-unsaturated amides to form the desired β-cyanoamides. Herein we describe a novel two-step approach to prepare β-cyanoamides via the conjugate hydrocyanation of α,β-unsaturated aldehydes. To date we have demonstrated proof-of-concept for the synthesis of Weinreb amide 3 starting from the simple substrate 1-cylohexene-1-carboxaldehyde (1). We are currently optimizing reaction conditions for the conjugate hydrocyanation of compound 1 using GC-MS analysis of reaction aliquots, and the results of this work are presented.

Investigations of the conjugate hydrocyanation of α,β-unsaturated aldehydes in organic synthesis

249th National Meeting (2015)

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