%0 Journal Article
%T ¦Á(¦Ä')-Michael Addition of Alkyl Amines to Dimethyl (E)-hex-2-en-4-ynedioate: Synthesis of ¦Á,¦Â-Dehydroamino Acid Derivatives
%A Arjun S. Chavan
%A Jie-Cheng Deng
%A Shih-Ching Chuang
%J Molecules
%D 2013
%I MDPI AG
%R 10.3390/molecules18032611
%X The direct nucleophilic addition of alkyl amines to the ¦Á(¦Ä')-carbon atom of dimethyl ( E)-hex-2-en-4-ynedioate to generate ¦Á,¦Â-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the ¦Á-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.
%K ¦Á-Michael addition
%K conjugated enyne
%K dehydroamino acids
%U http://www.mdpi.com/1420-3049/18/3/2611