Synthesis 2016; 48(12): 1927-1933
DOI: 10.1055/s-0035-1561604
special topic
© Georg Thieme Verlag Stuttgart · New York

Gold-Catalyzed Dimeric Cyclization of Isoeugenol and Related 1-Phenylpropenes in Ionic Liquid: Environmentally Friendly and Stereoselective Synthesis of 1,2,3-Trisubstituted 2,3-Dihydro-1H-indenes

Nobuyoshi Morita*
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Rie Mashiko
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Dai Hakuta
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Daisuke Eguchi
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Shintaro Ban
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Yoshimitsu Hashimoto
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Iwao Okamoto
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Osamu Tamura*
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
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Publikationsverlauf

Received: 30. Januar 2016

Accepted after revision: 09. März 2016

Publikationsdatum:
20. April 2016 (online)


Abstract

Gold-catalyzed dimerization of isoeugenol and related 1-phenylpropenes in ionic liquid enabled environmentally friendly, stereo­selective synthesis of 1,2,3-trisubstituted 2,3-dihydro-1H-indenes. Dimerization of isoeugenol or isohomogenol afforded diisoeugenol or diisohomogenol, respectively, with α-configuration, whereas dimerization of α-asarone furnished diasarone with γ-configuration.

Supporting Information

 
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