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?(?')-Michael addition of alkyl amines to dimethyl (E)-hex-2-en-4-ynedioate: synthesis of ?,?-dehydroamino acid derivatives.

ABSTRACT: The direct nucleophilic addition of alkyl amines to the ?(?')-carbon atom of dimethyl (E)-hex-2-en-4-ynedioate to generate ?,?-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the ?-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.

SUBMITTER: Chavan AS

PROVIDER: S-EPMC6270175 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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α(δ')-Michael addition of alkyl amines to dimethyl (E)-hex-2-en-4-ynedioate: synthesis of α,β-dehydroamino acid derivatives.

Chavan Arjun S AS Deng Jie-Cheng JC Chuang Shih-Ching SC

Molecules (Basel, Switzerland) 20130227 3

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)- ...[more]

PMID: 23446918

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