A Convenient Conversion of Terminal Alkenes into Homologous Unsaturated and Doubly Unsaturated Esters

Unsaturated and doubly unsaturated esters have been synthesized in two steps by the application of a radical xanthate transfer process of a simple methylsulfoxide starting material to a range of terminal alkenes. syn-Elimination of the sulfoxide gives α,β-unsaturated esters, which coupled with a xan...

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Veröffentlicht in:Organic letters 2012-02, Vol.14 (4), p.1020-1023
Hauptverfasser: Hawkins, Bill, Paddock, Victoria L, Tölle, Nina, Zard, Samir Z
Format: Artikel
Sprache:eng
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Zusammenfassung:Unsaturated and doubly unsaturated esters have been synthesized in two steps by the application of a radical xanthate transfer process of a simple methylsulfoxide starting material to a range of terminal alkenes. syn-Elimination of the sulfoxide gives α,β-unsaturated esters, which coupled with a xanthate elimination yields α,β,γ,δ-unsaturated esters.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol203387r