The direct nucleophilic addition of alkyl amines to the α(δ')-carbon atom of dimethyl ( E)-hex-2-en-4-ynedioate to generate α,β-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the α-selective nucleophilic conjugate addition to conjugated dimethyl ( E)-hex-2-en-4-ynedioate. The reaction with primary alkyl amines gives only the (2 E,4 E)-stereoisomer, while that with secondary alkyl amines gives the (2 E,4 E) and (2 Z,4 E)-stereoisomers of dimethyl (2-alkylamino)-muconic ester.
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