title: 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.
authors: Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan.
authors: Arjun S
authors: AS
authors: Chavan
authors: Jie-Cheng
authors: JC
authors: Deng
authors: Shih-Ching
authors: SC
authors: Chuang
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002625:Chemistry, Organic
chemical_list: D000588:Amines; D000596:Amino Acids