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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 22, Number 12
BKCSDE 22(12)
December 20, 2001 

A Convenient Allylation of 1,n-Dicarbonyl Compounds Using Organoindium Reagents
Phil Ho Lee, Dong Seomoon, Kooyeon Lee
Indium, Allylindium reagent, Hydroxy unsaturated carbonyl compounds, Chemoselectivity.
The chemoselective reactions of 1,n-dicarbonyl compounds with allyl halides using indium metal were investigated. α-Ketoesters such as ethyl pyruvate, ethyl 3-methyl-2-oxobutyrate and ethyl benzoylformate reacted with a variety of allyl halides in the presence of indium to afford hydroxy unsaturated carbonyl compounds in good to excellent yields in MeOH/HCl at 25℃. For the allyl bromide, the presence of various substituents at the α or γ position exhibited little effects on both the reaction rates and yields. Ethyl acetoacetate or ethyl levulinate was treated with allylindium reagent to give hydroxy unsaturated carbonyl compounds in good yield. These results mean that both reactivity and selectivity are independent of the distance between carbonyl groups. 2,3-Butanedione or 1-phenyl-1,2-propanedione reacted with allylindium to produce monoallylation product as major compound.
1380 - 1384
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