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Gold‐Catalyzed Rearrangement of Allylic Oxonium Ylides: Efficient Synthesis of Highly Functionalized Dihydrofuran‐3‐ones
Author(s) -
Fu Junkai,
Shang Hai,
Wang Zhaofeng,
Chang Le,
Shao Wenbing,
Yang Zhen,
Tang Yefeng
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201208305
Subject(s) - oxonium ion , allylic rearrangement , claisen rearrangement , diazo , sigmatropic reaction , chemistry , catalysis , rearrangement reaction , ylide , cope rearrangement , medicinal chemistry , combinatorial chemistry , organic chemistry , ion
“Diazo” not needed : The title reaction results in the rearrangement of oxonium ylides, which were prepared from readily available homopropargylic allylic ethers instead of diazo compounds, through two different mechanisms: a concerted 2,3‐sigmatropic rearrangement, or a stepwise 1,4‐allyl migration followed by a Claisen rearrangement (see scheme).