Chemical & Pharmaceutical Bulletin 2002-03-01

New entry of coupling reaction of phenacylamine derivatives with silylstannane.

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

Index: Chem. Pharm. Bull. 50(3) , 441-3, (2002)

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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.