New Entry of Coupling Reaction of Phenacylamine Derivatives with Silylstannane

Yasumasa Iwai; Kumiko Kita; Yoko Matsushita; Aiko Yamauchi; Masaru Kihara

doi:10.1248/cpb.50.441

Notes

New Entry of Coupling Reaction of Phenacylamine Derivatives with Silylstannane

Yasumasa Iwai, Kumiko Kita, Yoko Matsushita, Aiko Yamauchi, Masaru Kihara

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Keywords: coupling reaction, enolate, silylstannane, phenacylamine

JOURNAL FREE ACCESS

2002 Volume 50 Issue 3 Pages 441-443

DOI https://doi.org/10.1248/cpb.50.441

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Abstract

The new coupling reaction of phenacylamines with silylstannane and lithium diisopropylamide (LDA) is reported. The treatment of a phenacylamine iodide 1 with (trimethylsilyl)tributylstannane (Me₃SiSnBu₃) and cesium fluoride (CsF) gave a dimerization product 2 having no iodine atom. Reaction of 1 with LDA afforded a dimerization product 3 with an iodine atom. The products 2 and 3 were separated to the meso and racemic isomers, respectively.

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