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Chelation-controlled regio- and stereoselective allylindation of norbornenols

✍ Scribed by Shuki Araki; Toshiya Kamei; Yukimitsu Igarashi; Tsunehisa Hirashita; Hatsuo Yamamura; Masao Kawai

Book ID
104262333
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
232 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first allylindation of norbornenoi derivatives has been realised highly regio-and stereoselectively. The reactions of allylindium sesquiiodide with syn-bicyclo[2.2.1 ]hept-2-en-7-oi and endo-bicyclo[2.2.1 ]hept-5-en-2ol gave ailylated 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.

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