Chelation-controlled regio- and stereoselective allylindation of norbornenols

被引:17
作者
Araki, S [1 ]
Kamei, T [1 ]
Igarashi, Y [1 ]
Hirashita, T [1 ]
Yamamura, H [1 ]
Kawai, M [1 ]
机构
[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
allylation; chelation; indium; indium compounds; metalation;
D O I
10.1016/S0040-4039(99)01552-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first allylindation of norbornenol derivatives has been realised highly regio- and stereoselectively. The reactions of allylindium sesquiiodide with syn-bicyclo[2.2.1]hept-2-en-7-ol and endo-bicyclo[2.2.1]hept-5-en-2-ol gave allylated products together with iodinated and oxygenated compounds. The product distribution could be controlled by changing the reaction solvent. In these reactions, the regio- and stereochemistry of the addition of the allylindium reagent is highly regulated via the chelation with the neighbouring hydroxyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7999 / 8002
页数:4
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