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

Arjun S. Chavan, Jie Cheng Deng, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

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.

Original languageEnglish
Pages (from-to)2611-2622
Number of pages12
JournalMolecules
Volume18
Issue number3
DOIs
StatePublished - 1 Mar 2013

Keywords

  • Conjugated enyne
  • Dehydroamino acids
  • α-Michael addition

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