Abstract

A new three-component coupling protocol, exploiting 2-bromoallyltrimethylsilane as a bifunctional linchpin, has been developed. The reaction sequence entails the following steps: lithiation of the vinyl bromide, addition of an aromatic or aliphatic aldehyde, execution of a solvent controlled 1,4-Brook rearrangement induced by HMPA to generate an allyl anion, and addition of a reactive second electrophile. Yields are moderate to good.

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