期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 356, 期 11-12, 页码 2417-2421出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400247
关键词
carbocyclization; gold; ipso-Friedel-Crafts alkenylation; spiro compounds; synthetic methods
资金
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- Chiba University
- Grants-in-Aid for Scientific Research [23390003] Funding Source: KAKEN
We have developed a novel synthetic method to furnish spiro[4.5]cyclohexadienones using an gold-catalyzed carbocyclization of phenols with a terminal alkyne via an intramolecular ipso-Friedel-Crafts alkenylation. Using 2-5 mol% of gold catalyst, 1 equiv. of methanesulfonic acid, and 1 equiv. of 2,6-di-tert-butylpyridine, a variety of spiro[4.5]cyclohexadienone derivatives with an exocyclic olefin unit was obtained in good to excellent yields. The divergent synthesis of dihydronaphthalene derivatives was also examined based on the newly developed gold catalysis.
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