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Rhenium( I )‐Catalyzed Intramolecular Geminal Carbofunctionalization of Alkynes: Tandem Cyclization of ω‐Acetylenic Dienol Silyl Ethers
Author(s) -
Kusama Hiroyuki,
Yamabe Hokuto,
Onizawa Yuji,
Hoshino Takahiko,
Iwasawa Nobuharu
Publication year - 2005
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.200461559
Subject(s) - geminal , rhenium , silylation , intramolecular force , alkyne , tandem , enol , chemistry , catalysis , medicinal chemistry , annulation , organic chemistry , stereochemistry , materials science , composite material
Bicycle production : The low‐valent rhenium complex [ReCl(CO) 5 ] catalyzes a tandem intramolecular cyclization reaction of ω‐acetylenic dienol silyl ethers. The alkyne undergoes a geminal carbofunctionalization in the presence of 0.5–3.0 mol % [ReCl(CO) 5 ] under photoirradiation to give bicyclic enol silyl ethers in high yields (see scheme, TIPS=triisopropylsilyl).