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Regioselective Addition Reactions of the Organoindium Reagents onto α,β-Unsaturated Ketones
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  • Regioselective Addition Reactions of the Organoindium Reagents onto α,β-Unsaturated Ketones
  • Regioselective Addition Reactions of the Organoindium Reagents onto α,β-Unsaturated Ketones
저자명
Lee. Phil-Ho,Kim. Hyun,Lee. Koo-Yeon,Seomoon. Dong,Kim. Sun-Dae,Kim. Hee-Chul,Kim. Hyun-Seok,Lee. Mi-Ae,Shim. Eun-Kyong,Lee. Seo
간행물명
Bulletin of the Korean Chemical Society
권/호정보
2004년|25권 11호|pp.1687-1691 (5 pages)
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대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

Regioselectivity on the reactions of ${alpha},{eta}$--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 ${alpha},{eta}$-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.