Gold‐Catalyzed Rearrangement of Allylic Oxonium Ylides: Efficient Synthesis of Highly Functionalized Dihydrofuran‐3‐ones | Zendy

Fu Junkai | Zendy; Shang Hai | Zendy; Wang Zhaofeng | Zendy; Chang Le | Zendy; Shao Wenbing | Zendy; Yang Zhen | Zendy; Tang Yefeng | Zendy

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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).

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