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Synthesis 2015; 47(15): 2223-2232
DOI: 10.1055/s-0034-1378856
DOI: 10.1055/s-0034-1378856
special topic
Nucleophilic Conjugate 1,5-Addition of Gilman Reagents to (E)-Hex-2-en-4-ynedioates: An Access to β(γ′)-Substituted Muconates
Authors
Further Information
Publication History
Received: 31 March 2015
Accepted after revision: 05 June 2015
Publication Date:
15 July 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
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378856.
- Supporting Information (PDF)
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