Tetrahedron letters

Allylic tin (IV)-tin (II) chloride-acetonitrile as a novel system for allylation of carbonyls or imines

M Yasuda, Y Sugawa, A Yamamoto, I Shibata, A Baba

Index: Yasuda, Makoto; Sugawa, Yoshihiro; Yamamoto, Akihiro; Shibata, Ikuya; Baba, Akio Tetrahedron Letters, 1996 , vol. 37, # 33 p. 5951 - 5954

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Citation Number: 35

Abstract

Effective allylation of aldehydes, ketones and imines was accomplished by allylic tributyltins 1 in the presence of SnCl2 in an acetonitrile solution. In this reaction system. Sn (IV) Sn (II) transmetallation must play a key role, generating the allylic tin (II) reagents as a novel reacting species. Acetonitrile effectively promoted the transmetallation to give anti-adducts in the reaction with cinnamyltin 1c, whereas dichloromethane disturbed the transmetallation ...

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