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

Autor: Tzu-Ting Kao, Ying-Chieh Wong, Kak-Shan Shia, Ming-Chen Chou, Yi-Wun Jhang, Jing-Kai Huang
Rok vydání: 2014
Předmět:
Zdroj: Advanced Synthesis & Catalysis. 356:3025-3038
ISSN: 1615-4150
DOI: 10.1002/adsc.201400257
Popis: 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.
Databáze: OpenAIRE
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