Browsing by Author "Chavan, Arjun S."

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alpha(delta ')-Michael Addition of Alkyl Amines to Dimethyl (E)-hex-2-en-4-ynedioate: Synthesis of alpha,beta-Dehydroamino Acid Derivatives
(2013-03-01)
Chavan, Arjun S.
;
Deng, Jie-Cheng
;
Chuang, Shih-Ching
;
應用化學系
;
Department of Applied Chemistry
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.
Nucleophilic Conjugate 1,5-Addition of Gilman Reagents to (E)-Hex-2-en-4-ynedioates: An Access to ()-Substituted Muconates
(2015-08-01)
Tai, Hung-Che
;
Chavan, Arjun S.
;
Chuang, Shih-Ching
;
應用化學系
;
Department of Applied Chemistry
An unusual nucleophilic conjugate addition of organocuprates to enynedioates resulted in chemo- and regioselective formation of ()-addition products, rather than ()-addition products, in moderate to good yields. This addition pattern is different from that with organophosphanes or alkyl amines, and presents a short and efficient method for the preparation of various ()-alkyl- or -aryl-substituted muconates compared with other synthetic approaches.