標題: alpha(delta ')-Michael Addition of Alkyl Amines to Dimethyl (E)-hex-2-en-4-ynedioate: Synthesis of alpha,beta-Dehydroamino Acid Derivatives
作者: Chavan, Arjun S.
Deng, Jie-Cheng
Chuang, Shih-Ching
應用化學系
Department of Applied Chemistry
關鍵字: alpha-Michael addition;conjugated enyne;dehydroamino acids
公開日期: 1-Mar-2013
摘要: The direct nucleophilic addition of alkyl amines to the alpha(delta')-carbon atom of dimethyl (E)-hex-2-en-4-ynedioate to generate alpha,beta-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the alpha-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.
URI: http://dx.doi.org/10.3390/molecules18032611
http://hdl.handle.net/11536/21745
ISSN: 1420-3049
DOI: 10.3390/molecules18032611
期刊: MOLECULES
Volume: 18
Issue: 3
起始頁: 2611
結束頁: 2622
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