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

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 45期

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

页码：7999 / 8002

页数：4

共 20 条

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