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Synthetically Useful Wagner–Meerwein Rearrangement of α‐Quaternary β‐Bromovinyl Methyl Ethers
Author(s) -
Wang AiXia,
Tu YongQiang,
Song ZhenLei,
Yuan DaoYi,
Hu XiangDong,
Wang ShaoHua,
Gao ShuanHu
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600195
Subject(s) - chemistry , tandem , cope rearrangement , alkylation , aryl , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , alkyl , materials science , composite material
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)