| Photoreactions of bicyclic aziridines with alkenes and alkynes: a novel synthetic methodology for 8-azabicyclo[3.2.1]octane derivatives. | |
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MedLine Citation:
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PMID: 18698479 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The photochemical C-C bond cleavage of bicyclic aziridines 7 and subsequent [3 + 2] cycloaddition with electron-deficient alkenes and alkynes afforded the novel head-to-head adducts selectively and efficiently. The adducts contain the naturally occurring 8-azabicyclo[3.2.1]octane skeleton (e.g. tropane alkaloids). The aziridine 8 fused with a 6-membered ring also afforded the cycloadducts but in poor yields. The methylaziridine 9 reacted with an electron-deficient alkene, affording the head-to-tail adduct 23 in addition to head-to-head adducts 22a and 22b. The photoreactions of bicyclic aziridines with alkenes and alkynes indicate a similar behavior to that of aziridines with a linear chain. |
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Authors:
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Keitaro Ishii; Motohiro Kido; Masahiro Noji; Shigeo Sugiyama |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-07-10 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 6 ISSN: 1477-0539 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2008 Sep |
Date Detail:
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Created Date: 2008-08-13 Completed Date: 2008-11-17 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 3186-95 Citation Subset: IM |
Affiliation:
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Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan. ishiikei@my-pharm.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkenes
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chemistry* Alkynes / chemistry* Aziridines / chemistry* Bicyclo Compounds / chemical synthesis*, chemistry Cyclization Magnetic Resonance Spectroscopy Models, Chemical Photochemistry* Tropanes / chemical synthesis, chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Alkenes; 0/Alkynes; 0/Aziridines; 0/Bicyclo Compounds; 0/Tropanes; 151-56-4/aziridine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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