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题名: BrOnsted Acid-Mediated Annulation of -Oxo Ketene Dithioacetals with Pyrroles: Efficient Synthesis of Structurally Diverse Cyclopenta[b]pyrroles
作者: Yang, Xiaoge1;  Wu, Kaikai1;  Wu, Ping1;  Chen, Jiping1;  Sun, Chenglin1;  Yu, Zhengkun1, 2
关键词: annulation ;  BrOnsted acids ;  pyrroles ;  synthetic methods ;  thioacetals
刊名: CHEMISTRY-A EUROPEAN JOURNAL
发表日期: 2015-06-22
DOI: 10.1002/chem.201501022
卷: 21, 期:26, 页:9323-9327
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
英文摘要: BrOnsted acid-mediated annulation of internal olefins -oxo ketene dithioacetals to pyrroles was efficiently achieved to afford cyclopenta[b]pyrroles. A pair of BrOnsted acids with acid strengths, that is, trifluoroacetic acid, and para-toluenesulfonic acid hydrate, were applied to promote the annulation reactions. The resultant products were readily oxidized to sulfones by meta-chloroperoxybenzoic acid. Subsequent treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene gave desulfurized terminal olefins or [2+2] cycloaddition products from the desulfurized olefin intermediates. The present protocol provides facile access to structurally diverse cyclopenta[b]pyrrole derivatives under mild conditions.
关键词[WOS]: H BOND ACTIVATION ;  ROSEOPHILIN ;  CYCLOADDITION ;  DERIVATIVES ;  ALKALOIDS ;  CHEMISTRY ;  EXPANSION ;  AMINES
语种: 英语
WOS记录号: WOS:000356795000007
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/146340
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

Recommended Citation:
Yang, Xiaoge,Wu, Kaikai,Wu, Ping,et al. BrOnsted Acid-Mediated Annulation of -Oxo Ketene Dithioacetals with Pyrroles: Efficient Synthesis of Structurally Diverse Cyclopenta[b]pyrroles[J]. CHEMISTRY-A EUROPEAN JOURNAL,2015,21(26):9323-9327.
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