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Nickel-catalyzed regioselective allylation of allylic alcohols

✍ Scribed by Akira Yanagisawa; Nobuyoshi Nomura; Shigeki Habaue; Hisashi Yamamoto

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
147 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

Regioselective allylmetallation of allylic alcohol has been accomplished by treatment with allylzinc in the presence of a nickel catalyst. Benzylic protective group of allyl alcohol facilitates the allylmetallation.

During the past two decades many investigations in the field of allylmetallation of alkenes using allylic Grignard reagents or zinc reagents have been reported. 1 For example, unsymmetrical allylic metal compounds added to 1-alkene are known to give the product (y--C-2) in eq. I. la We have recently shown that an ct,13unsaturated acetal undergoes rapid metallation upon treatment with allylzinc in the presence of nickel catalyst. 2

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