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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 01期

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

页码：172 / 177

页数：6

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