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Synthesis of Nine‐Membered Carbocycles by the [4+3+2] Cycloaddition Reaction of Ethyl Cyclopropylideneacetate and Dienynes
Author(s) -
Saito Shinichi,
Maeda Kyotaro,
Yamasaki Ryu,
Kitamura Takuya,
Nakagawa Minami,
Kato Korehito,
Azumaya Isao,
Masu Hyuma
Publication year - 2010
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.200907052
Subject(s) - cycloaddition , chemistry , scheme (mathematics) , computer science , information retrieval , combinatorial chemistry , stereochemistry , organic chemistry , mathematics , catalysis , mathematical analysis
Various dienynes reacted efficiently with ethyl cyclopropylideneacetate in the presence of [Ni(cod) 2 ]/PPh 3 , and cyclononadienes were synthesized in a selective manner. Dienynes tethered with aromatic rings were very good substrates, and the corresponding tricyclic compounds were isolated in high yields. The reaction provides a new route for the synthesis of nine‐membered carbocycles (see scheme).