Regioselective Addition Reactions of the Organoindium Reagents onto ¥á, ¥â-Unsaturated Ketones

Bulletin of the Korean chemical society

Sundae Kim¹  Miae Lee¹  Heechul Kim¹  Misook Kim¹  Dong Seomoon¹  Hyunseok Kim¹  Madabhushi Sridhar¹  Seokju Lee¹  Kooyeon Lee¹  Hyun Kim¹  Eunkyong Shim¹  Phil Ho Lee¹  Kwanghyun Noh¹  Mijeong Han¹ 

关键词: Regioselectivity;    Conjugate addition;    Allylindium;    Allenylindium;    Additive;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

Regioselectivity on the reactions of �?, �?-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 �?, �?-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 �?-methyl group gave allenylated product inBarbier type.

【 授权许可】

Unknown