Manganese(III)-Catalyzed Oxidative Cyclization of Aryl 1-Cyanoalk-5-ynyl Ketone Systems: A Convenient and General Approach to Cyclopenta[b]naphthalene Derivatives

A convenient and general approach for cyclopenta[b]naphthalene derivatives containing a structurally diverse functionality at C‐4 position has been successfully developed, whereby manganese(III) acetate plays a key role to facilitate the tandem 5‐exo‐dig and 6‐exo/endo cyclization in an efficient ma...

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Veröffentlicht in:Advanced synthesis & catalysis 2014-10, Vol.356 (14-15), p.3025-3038
Hauptverfasser: Wong, Ying-Chieh, Kao, Tzu-Ting, Huang, Jing-Kai, Jhang, Yi-Wun, Chou, Ming-Chen, Shia, Kak-Shan
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Sprache:eng
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Zusammenfassung:A convenient and general approach for cyclopenta[b]naphthalene derivatives containing a structurally diverse functionality at C‐4 position has been successfully developed, whereby manganese(III) acetate plays a key role to facilitate the tandem 5‐exo‐dig and 6‐exo/endo cyclization in an efficient manner. Various functional groups, including trimethyl silyl, aryl, ester, ketone, secondary/tertiary amide, phosphonate and halogen, capped on the terminal acetylenic unit are well tolerated under optimal reaction conditions. It is highly conceivable that this novel [6.6.5] framework formation procedure may have broad synthetic utility in light of its operational simplicity and high yields.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400257