Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methyleneindolinones
A simple route to complexity: An organocatalytic 1,3‐dipolar cycloaddition between azlactones and methyleneindolinones provided spirooxindoles with high enantioselectivity (see scheme). This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate....
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| Veröffentlicht in: | Angewandte Chemie International Edition 2013-08, Vol.52 (33), p.8633-8637 |
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| container_issue | 33 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Sun, Wangsheng Zhu, Gongming Wu, Chongyang Li, Guofeng Hong, Liang Wang, Rui |
| description | A simple route to complexity: An organocatalytic 1,3‐dipolar cycloaddition between azlactones and methyleneindolinones provided spirooxindoles with high enantioselectivity (see scheme). This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate. Bn=benzyl, HOBt=1‐hydroxy‐1H‐benzotriazole, MTBE=methyl tert‐butyl ether, PG=protecting group, TMS=trimethylsilyl. |
| doi_str_mv | 10.1002/anie.201302831 |
| format | Article |
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This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate. Bn=benzyl, HOBt=1‐hydroxy‐1H‐benzotriazole, MTBE=methyl tert‐butyl ether, PG=protecting group, TMS=trimethylsilyl.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201302831</identifier><identifier>PMID: 23818172</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>1,3‐dipolar cycloaddition ; 3-dipolar cycloaddition ; asymmetric synthesis ; Aza Compounds - chemistry ; azlactones ; Catalysis ; Complexity ; Cyclization ; Cycloaddition ; Cycloaddition Reaction ; Ethers ; Indoles - chemistry ; Lactones - chemistry ; Magnetic Resonance Spectroscopy ; methyleneindolinones ; Molecular Structure ; Nuclei ; organocatalysis ; Spiro Compounds - chemistry ; Stereoisomerism ; Transformations</subject><ispartof>Angewandte Chemie International Edition, 2013-08, Vol.52 (33), p.8633-8637</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5471-8e44093e088577069ac4b3034f28db0b2db6f9408e5f3ca65bb47940951ccd7c3</citedby><cites>FETCH-LOGICAL-c5471-8e44093e088577069ac4b3034f28db0b2db6f9408e5f3ca65bb47940951ccd7c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201302831$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201302831$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23818172$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sun, Wangsheng</creatorcontrib><creatorcontrib>Zhu, Gongming</creatorcontrib><creatorcontrib>Wu, Chongyang</creatorcontrib><creatorcontrib>Li, Guofeng</creatorcontrib><creatorcontrib>Hong, Liang</creatorcontrib><creatorcontrib>Wang, Rui</creatorcontrib><title>Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methyleneindolinones</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A simple route to complexity: An organocatalytic 1,3‐dipolar cycloaddition between azlactones and methyleneindolinones provided spirooxindoles with high enantioselectivity (see scheme). This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate. 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| subjects | 1,3‐dipolar cycloaddition 3-dipolar cycloaddition asymmetric synthesis Aza Compounds - chemistry azlactones Catalysis Complexity Cyclization Cycloaddition Cycloaddition Reaction Ethers Indoles - chemistry Lactones - chemistry Magnetic Resonance Spectroscopy methyleneindolinones Molecular Structure Nuclei organocatalysis Spiro Compounds - chemistry Stereoisomerism Transformations |
| title | Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methyleneindolinones |
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