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ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 25, Number 11
BKCSDE 25(11)
November 20, 2004 |
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Title |
Regioselective Addition Reactions of the Organoindium Reagents onto α, β-Unsaturated Ketones
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Author |
Phil Ho Lee*, Hyun Kim, Kooyeon Lee, Dong Seomoon, Sundae Kim, Heechul Kim, Hyunseok Kim, Miae Lee, Eunkyong Shim, Seokju Lee, Misook Kim, Mijeong Han, Kwanghyun Noh, Madabhushi Sridhar
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Keywords |
Regioselectivity, Conjugate addition, Allylindium, Allenylindium, Additive
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Abstract |
Regioselectivity on the reactions of α, β-enones with organoindium such as in situ generated allylindium and allenylindium was systematically studied in the presence of TMSCl as an additive. Treatment of 2-cyclohexen-1-one, carvone, 2-cyclohepten-1-one, and chalcone with allylindium reagent produced 1,4-addition products in good yields, while 2-cyclopenten-1-one, 2-methyl-2-cyclopenten-1-one, 4,4-dimethylcyclohexen-1-one, 3-nonen-2-one, 4-hexen-3-one, and 4-phenyl-3-buten-2-one afforded 1,2-addition products. Indium reagent derived from indium and propargyl bromide in Grignard type gave addition products in good yields, under which the successive addition of α, β-enone and TMSCl were necessary. Although organoindium reagent derived from propargyl bromide produced propargylated compound in Grignard type except 2-cyclohepten-1-one, indium reagent obtained from 1-bromo-2-butyne having γ-methyl group gave allenylated product inBarbier type.
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Page |
1687 - 1691 |
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