Synthesis 2015; 47(15): 2223-2232
DOI: 10.1055/s-0034-1378856
special topic
© Georg Thieme Verlag Stuttgart · New York

Nucleophilic Conjugate 1,5-Addition of Gilman Reagents to (E)-Hex-2-en-4-ynedioates: An Access to β(γ′)-Substituted Muconates

Hung-Che Tai
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan   eMail: jscchuang@faculty.nctu.edu.tw
,
Arjun S. Chavan
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan   eMail: jscchuang@faculty.nctu.edu.tw
,
Shih-Ching Chuang*
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan   eMail: jscchuang@faculty.nctu.edu.tw
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Publikationsverlauf

Received: 31. März 2015

Accepted after revision: 05. Juni 2015

Publikationsdatum:
15. Juli 2015 (online)


Abstract

An unusual nucleophilic conjugate addition of organocu­prates to enynedioates resulted in chemo- and regioselective formation of β(γ′)-addition products, rather than α(δ′)-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 β(γ′)-alkyl- or -aryl-substituted muconates compared with other synthetic approaches.

Supporting Information