Facile synthesis of homoallylamines via α-regioselectivity in ultrasonic mediation and γ-adduct syn-stereoselective allylation with AlCl3-catalysis.

[Display omitted] • Versatile Synthesis of Homoallylamines: This study presents efficient methods for the synthesis of homoallylamines, which are valuable precursors in the formation of bioactive N -heterocycles, such as pyrrolidines and β-lactams. • Regioselective Allylation: The research demonstrates the regioselective allylation of aldimines with allyl metal reagents under sonochemical Barbier-type reaction conditions and AlCl3 catalysis, achieving both α-adduct and γ-adduct formations. • High Regio- and Stereoselectivity: Optimized reaction conditions lead to high regio- and stereoselectivity, with ultrasonic-mediated conditions favoring α-adducts and AlCl3 catalysis promoting γ-adducts. • Substrate Scope and Functional Group Compatibility: The methods exhibit broad substrate scope, accommodating various aldimines with different substituents, including phenyl, tosyl, and heteroaromatic groups, yielding products in moderate to good yields with excellent regioselectivity. • Mechanistic Insights: Proposed mechanisms for both the sonochemical and AlCl3-catalyzed processes explain the observed regioselectivity and diastereoselectivity, highlighting the role of zinc activation and Lewis acid catalysis in facilitating the reactions. The allylation reaction of aldimines with allyl metal reagents is an important synthetic method for the preparation of homoallylamines. Therefore, we wish to report a highly regioselective and stereoselective allylation reaction under sonochemical Barbier-type reaction conditions. The high yields of regioselective α-adducts were achieved by reacting cinnamyl bromide, zinc, 1,2-dibromoethane, and aldimine in THF under sonochemical Barbier-type conditions. Highly regioselective and stereoselective allylation reactions were also achieved under Lewis acid-promoted Barbier-type reaction conditions. [ABSTRACT FROM AUTHOR]