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Indium-mediated nucleophilic substitution reaction of β,γ-unsaturated α-methoxypiperidine derivative in water

✍ Scribed by Yoshihiro Matsumura; Osamu Onomura; Hideaki Suzuki; Shigeru Furukubo; Toshihide Maki; Chao-Jun Li

Book ID
104253746
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
113 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Water as a solvent was found to accelerate the indium-mediated Barbier type allylation and benzylation of b,g-unsaturated piperidinium ion which was generated from b,g-unsaturated a-methoxy-N-methoxycarbonylpiperidine, while ring-opened allylated product was obtained in a case using b,g-saturated a-methoxy-N-methoxycarbonylpiperidine. Other solvents than water resulted in low yield of the allylated and benzylated products, suggesting that water is essential to generate the piperidinium ion intermediate from b,g-unsaturated a-methoxy-N-methoxycarbonylpiperidine.

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