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Synthesis of Cyclobutanones via Gold‐Catalyzed Oxidative Rearrangement of Homopropargylic Ethers
Author(s) -
Xu Mei,
Ren TianTian,
Wang KaiBing,
Li ChuanYing
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300227
Subject(s) - chemistry , oxonium ion , carbenoid , ylide , catalysis , ether , ring (chemistry) , medicinal chemistry , silyl ether , stereochemistry , organic chemistry , silylation , ion , rhodium
In the presence of a gold catalyst and 8‐ethylquinoline N ‐oxide, a homopropargylic ether bearing an electron‐rich aromatic ring or an alkenyl group can be converted into a cis ‐cyclobutanone smoothly. An α‐oxo gold carbenoid is proved to be the key intermediate, and it can evolve into an oxonium ylide.