Preparation of gamma-Heterosubstituted Allylindium and Diindium Reagents and Their Reactions with Carbonyl Compounds.
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-ol. 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.
Hirashita
Tsunehisa
T
Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan.
Kamei
Toshiya
T
Horie
Tomoaki
T
Yamamura
Hatsuo
H
Kawai
Masao
M
Araki
Shuki
S