Alkylative Amination of Non-enolizable Aldehydes with Alkyl(dialkylamino)titanium Derivatives

Article abstract of DOI:10.1002/hlca.19820650831

The readily available tris(diethylamino)methyltitanium and related compounds (see 1 in Scheme 2) react with non-enolizable aldehydes to give tertiary amines 2; these amines result from direct replacement of the carbonyl O-atom by an alkyl and an amino group (Scheme 3).A tentative mechanism is proposed, according to which the amino group is transferred to the carbonyl C-atom prior to the alkyl group (Scheme 4).