α(δ')-Michael Addition of Alkyl Amines to Dimethyl (E)-hex-2-en-4-ynedioate: Synthesis of α,β-Dehydroamino Acid Derivatives

Abstract

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 (2E,4E)-stereoisomer, while that with secondary alkyl amines gives the (2E,4E) and (2Z,4E)-stereoisomers of dimethyl (2-alkylamino)-muconic ester.

Keywords

• α-Michael addition
• conjugated enyne
• dehydroamino acids