The combination of Pd catalyst and diethylzinc with triethylborane promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine rings are applicable for the synthesis of isoquinoline derivatives via the Diels-Alder reaction followed by an oxidation reaction with DDQ.

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Palladium-Catalyzed [4 + 2] Cycloaddition of Aldimines and 1,4-Dipolar Equivalents via AmphiphilicAllylation. -The title reaction is promoted by diethylzinc. The aldimines are synthesized from aldehydes and amines by azeotropic distillation and are further used in the [4+2] cycloaddition without isolation. This is the first example of the amphiphilic allylation of aldimines with bis allylic moieties. The products [e.g. (IV), (VI), etc.] can be applied for the synthesis of isoquinoline derivatives [e.g. (IX)]. -(HIRATA, G.; YAMADA, N.; SANADA, S.; ONODERA, G.; KIMURA*, M.; Org. Lett. 17 (2015) 3, 600-603, http://dx.doi.org/10.1021/ol503614d ; Grad. Sch. Eng., Nagasaki Univ., Nagasaki 852, Japan; Eng.) -L. Grundl 25-186

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