Abstract

One-shot treatment of a mixture of Danishefsky diene 4 and tetraallyltin 8 with 3-formylbenzylidene imines 1 in the presence of Sc(OTf)3 catalyst provides a single product 13 as a result of exclusive Diels–Alder and allylation reactions on the imine and aldehyde functions, respectively. The chemoselectivities of the respective elementary reactions are improved in the parallel reaction, and the redistribution of substrate 1 that is induced readily by Sc(OTf)3 is completely suppressed, thus offering a novel protocol for simplification of the multi-step chemical process.

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