Preparation of γ-heterosubstituted allylindium and diindium reagents and their reactions with carbonyl compounds

被引:40
作者
Hirashita, T [1 ]
Kamei, T [1 ]
Horie, T [1 ]
Yamamura, H [1 ]
Kawai, M [1 ]
Araki, S [1 ]
机构
[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
D O I
10.1021/jo9816111
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various gamma-heteroatom-substituted allylindium reagents were prepared, and their reactions with carbonyl compounds were examined. The reaction of 1,3-dibromopropene with metallic indium gave two types of organoindium species, gamma-bromoallylindium and allylic diindium reagents. While the former gave 2-phenyl-3-vinyloxirane upon the coupling with benzaldehyde, the latter gave 1-phenylbut-3-en-1-o1. 1-Iodo-3-bromopropene gave the homoallylic alcohol exclusively. gamma-Alkoxyallylindium reagents were prepared by treating the corresponding gamma-alkoxyallyllithium with indium trichloride and reacted with benzaldehyde to give vic-diol mono ethers in high yields with good syn selectivity. gamma-(Trimethylsilyl)allylindium and alpha,gamma-disubstituted allylindium reagents were also prepared via transmetalation with the corresponding allyllithium.
引用
收藏
页码:172 / 177
页数:6
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