Homoallylic benzoylhydrazines

It was also found that in the presence of a catalytic amount of Sc(OTf)3 benzoylhydrazones reacted with tetraallyltin to afford the corresponding homoallylic hydrazines these were readily converted to homoallylic amines. Three-component reactions of aldehydes, benzoylhydrazine, and tetraallyltin also proceeded smoothly in the presence of a catalytic amount of Sc(OTf)3 [15]. 

While allylation of imines is also catalyzed by Sc(OTf)3 in dichloromethane to give homoallylic amines in moderate yield, three-component reactions of aldehydes, amines, and allyltribut-yltin proceed in micellar systems to afford the corresponding homoallylic amines in good to high yield (eq 12). It is suggested that imine formation from aldehydes and amines is very fast under these conditions, and that the selective activation of imines rather than aldehydes is achieved. Allylation of (V-benzoylhydrazone or three-component reaction of aldehydes, benzoylhydrazine, and tetraallyltin are also catalyzed by Sc(OTf)3. ... 

Synthesis of homoallylic alcohols through the reaction of organometallic allyl compounds with carbonyl compounds is one of the most important processes in organic synthesis. Sc(OTf)3-catalyzed allylation of aldehydes with tetraallyltin to prepare homoallylic alcohols has been reported. Recently, it was revealed that the addition of acetic anhydride to the reaction mixture dramatically increases the reaction s yields to more than 90% [10]. On the other hand, in the presence of a catalytic amount of Sc(OTf)3 (l-5mol%), benzoylhydrazines reacted with tetraallyltin to give the corresponding homoallylic hydrazines, which were readily converted to homoallylic amines (Scheme 12.6) [11]. Three-component reactions of aldehydes, benzoylhydrazine, and tetraallyltin also proceeded smoothly in the presence of a catalytic amount of Sc(OTf)3. 

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See also in sourсe #XX -- [ ]

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