Three-Component Synthesis of Homoallylic Amines Promoted by Carboxylic Acids

Abstract

A highly selective, three-component reaction promoted by carboxylic acids for the synthesis of homoallylic amines has been developed. By using maleic acid or trifluoroacetic acid as a promoter, the reaction between a variety of aldehydes, aromatic amines, and allyltin reagents proceeds smoothly to afford the corresponding homoallylic amines in moderate to quantitative yields under mild conditions.

Key words

allylations - carboxylic acids - imines - multicomponent reactions - tin

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9

Benzaldehyde (16 mg, 0.15 mmol), aniline (14 mg, 0.15 mmol), and maleic acid (18 mg, 0.15 mmol) were added successively to CD₃CN (0.5 mL), and the mixture was monitored by ¹H NMR. It was obvious that the corresponding iminium salt was produced and aniline had disappeared completely.