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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 25, Number 11
BKCSDE 25(11)
November 20, 2004 

Regioselective Addition Reactions of the Organoindium Reagents onto α, β-Unsaturated Ketones
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
Regioselectivity, Conjugate addition, Allylindium, Allenylindium, Additive
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.
1687 - 1691
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