Synthetically Useful Wagner–Meerwein Rearrangement of α‐Quaternary β‐Bromovinyl Methyl Ethers

A synthetically useful Wagner–Meerwein (WM) rearrangement is reported in this paper. The investigation on the design and optimization involved the substrates α-quaternary β-bromovinyl methyl ethers as well as the reaction conditions. γ-Aryl α,β-unsaturated aldehydes with versatile synthetic uses could readily be obtained through a special pathway in high yields. For example, tricyclic aromatic systems were constructed efficiently through a tandem WM rearrangement/Friedel–Crafts alkylation.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)