Synthesis of the phenanthrene and cyclohepta[ a ]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes

Ming Chang P. Yeh, Ming Nan Lin, Yi Shiang Chou, Tern Chi Lin, Li Yu Tseng

研究成果: 雜誌貢獻期刊論文同行評審

8 引文 斯高帕斯(Scopus)

摘要

The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in good yields. This hydroarylation can be applied to the synthesis of perhydrocyclohepta[a]naphthalenes from aryl-tethered cycloheptadienes and the gold(I) catalyst.

原文英語
頁(從 - 到)4027-4033
頁數7
期刊Journal of Organic Chemistry
76
發行號10
DOIs
出版狀態已發佈 - 2011 五月 20

ASJC Scopus subject areas

  • 有機化學

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