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Molecules 2013, 18(3), 2611-2622; doi:10.3390/molecules18032611
Article

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

,  and *
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan
* Author to whom correspondence should be addressed.
Received: 31 December 2012 / Revised: 7 February 2013 / Accepted: 20 February 2013 / Published: 27 February 2013
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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 α-Michael addition; conjugated enyne; dehydroamino acids
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Chavan, A.S.; Deng, J.-C.; Chuang, S.-C. α(δ')-Michael Addition of Alkyl Amines to Dimethyl (E)-hex-2-en-4-ynedioate: Synthesis of α,β-Dehydroamino Acid Derivatives. Molecules 2013, 18, 2611-2622.

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