Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan.
Molecules. 2013 Feb 27;18(3):2611-22. doi: 10.3390/molecules18032611.
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.
本文报道了二甲基（E）-己-2-烯-4-炔二酸酯的α(δ')-碳原子与烷基伯胺的直接亲核加成，生成α,β-脱氢氨基酸衍生物。在此，我们研究了各种伯胺和仲胺在与共轭的二甲基（E）-己-2-烯-4-炔二酸酯的α-选择性亲核共轭加成中的反应性。与伯烷基胺的反应仅得到（2E,4E）-立体异构体，而与仲烷基胺的反应则得到二甲基（2-氨基烷基）-马来酸酯的（2E,4E）和（2Z,4E）-立体异构体。
