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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 (CC BY 3.0).

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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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