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Synthesis 2003(12): 1797-1802
DOI: 10.1055/s-2003-41035
DOI: 10.1055/s-2003-41035
PAPER
© Georg ThiemeVerlag Stuttgart · New York
Stereoselective Preparationof Functionalized Unsaturated Lactones and Esters via FunctionalizedMagnesium Carbenoids
Further Information
Received
3 June 2003
Publication Date:
13 August 2003 (online)
Publication History
Publication Date:
13 August 2003 (online)
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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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