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 to produce syn-adducts.
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