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BrOnsted Acid-Mediated Annulation of -Oxo Ketene Dithioacetals with Pyrroles: Efficient Synthesis of Structurally Diverse Cyclopenta[b]pyrroles
Yang, Xiaoge1; Wu, Kaikai1; Wu, Ping1; Chen, Jiping1; Sun, Chenglin1; Yu, Zhengkun1,2
KeywordAnnulation Bronsted Acids Pyrroles Synthetic Methods Thioacetals
Source PublicationCHEMISTRY-A EUROPEAN JOURNAL
2015-06-22
DOI10.1002/chem.201501022
Volume21Issue:26Pages:9323-9327
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordH BOND ACTIVATION ; ROSEOPHILIN ; CYCLOADDITION ; DERIVATIVES ; ALKALOIDS ; CHEMISTRY ; EXPANSION ; AMINES
AbstractBrOnsted 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.
Language英语
WOS IDWOS:000356795000007
Citation statistics
Cited Times:9[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/146340
Collection中国科学院大连化学物理研究所
Affiliation1.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
GB/T 7714
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.
APA Yang, Xiaoge,Wu, Kaikai,Wu, Ping,Chen, Jiping,Sun, Chenglin,&Yu, Zhengkun.(2015).BrOnsted Acid-Mediated Annulation of -Oxo Ketene Dithioacetals with Pyrroles: Efficient Synthesis of Structurally Diverse Cyclopenta[b]pyrroles.CHEMISTRY-A EUROPEAN JOURNAL,21(26),9323-9327.
MLA Yang, Xiaoge,et al."BrOnsted Acid-Mediated Annulation of -Oxo Ketene Dithioacetals with Pyrroles: Efficient Synthesis of Structurally Diverse Cyclopenta[b]pyrroles".CHEMISTRY-A EUROPEAN JOURNAL 21.26(2015):9323-9327.
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