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Rhenium‐Catalyzed Synthesis of Stereodefined Cyclopentenes from β‐Ketoesters and Aliphatic Allenes
Author(s) -
Yudha S. Salprima,
Kuninobu Yoichiro,
Takai Kazuhiko
Publication year - 2008
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.200803350
Subject(s) - allene , rhenium , stereoselectivity , ring (chemistry) , catalysis , chemistry , methylene , computer science , medicinal chemistry , organic chemistry
Come on allene : Commercially available [Re 2 (CO) 10 ] as a catalyst provides five‐membered carbocycles in moderate to excellent yields with high stereoselectivity (see scheme). The configuration at each of the three sp 3 carbon centers of the ring is defined. The reaction proceeds at the β, γ, and adjacent methylene positions of the allene; previously, similar reactions usually occurred at the α, β, and γ positions of the allene.