Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Regioselective Addition Reactions of the Organoindium Reagents onto α,β-Unsaturated Ketones

  • Lee, Phil-Ho (Department of Chemistry, Kangwon National University) ;
  • Kim, Hyun (Department of Chemistry, Kangwon National University) ;
  • Lee, Koo-Yeon (Department of Chemistry, Kangwon National University) ;
  • Seomoon, Dong (Department of Chemistry, Kangwon National University) ;
  • Kim, Sun-Dae (Department of Chemistry, Kangwon National University) ;
  • Kim, Hee-Chul (Department of Chemistry, Kangwon National University) ;
  • Kim, Hyun-Seok (Department of Chemistry, Kangwon National University) ;
  • Lee, Mi-Ae (Department of Chemistry, Kangwon National University) ;
  • Shim, Eun-Kyong (Department of Chemistry, Kangwon National University) ;
  • Lee, Seok-Ju (Department of Chemistry, Kangwon National University) ;
  • Kim, Mi-Sook (Department of Chemistry, Kangwon National University) ;
  • Han, Mi-Jeong (Department of Chemistry, Kangwon National University) ;
  • Noh, Kwang-Hyun (Department of Chemistry, Kangwon National University) ;
  • Sridhar, Madabhushi (Department of Chemistry, Kangwon National University)
  • Published : 2004.11.20
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Abstract

Regioselectivity on the reactions of ${\alpha},{\beta}$--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 ${\alpha},{\beta}$-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 ${\gamma}$-methyl group gave allenylated product inBarbier type.

Keywords

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