Stereoselective Preparationof Functionalized Unsaturated Lactones and Esters via FunctionalizedMagnesium Carbenoids

Viet Anh Vu; Ilan Marek; Paul Knochel

doi:10.1055/s-2003-41035

PAPER

Stereoselective Preparationof Functionalized Unsaturated Lactones and Esters via FunctionalizedMagnesium Carbenoids

Viet Anh Vu^a, Ilan Marek^b, Paul Knochel*^a
^a Department Chemie, Ludwig-Maximilians-UniversitätMünchen, Butenandtstrasse 5-13, 81377 München,Germany
Fax: +49(89)218077680 ; e-Mail: paul.knochel@cup.uni-muenchen.de;
^b Department of Chemistry, Technion-IsraelInstitute of Technology, Technion City, Haifa 32000,Israel
Fax: +972(4)8295703; e-Mail: chilanm@techunix.technion.ac.il;

Abstract

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Abstract

The reaction of β,β-dibromo or diiodo unsaturatedesters with i-PrMgCl (1 equivalent) indiethyl ether allows the generation of functionalized alkenylmagnesiumcarbenoids which react with retention of configuration with variouselectrophiles providing polyfunctionalized unsaturated esters andlactones. By using two equivalents of i-PrMgCl,a 1,2-migration with retention of configuration occurs in diethylether allowing a new synthesis of tetrasubstituted esters and lactones.

Key words

functionalized magnesium carbenoids - iodine-magnesiumexchange - cross-coupling - lactone synthesis - palladium catalysis

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References

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