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BF3-induced rearrangement of aziridinocyclopropanes derived from 2-phenylsulfonyl-1,3-dienes: A new approach to the tropane alkaloid skeleton
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
1996 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 37, no 19, 3371-3374 p.3371-3374 p.Article in journal (Refereed) Published
Abstract [en]

Five N-substituted derivatives of 1,2-methylene-3,4-aziridino 2-phenylsulfonyl cycloalkanes (3a-e) were prepared from their corresponding epoxy cyclopropanes via ring opening of the epoxide by sodium azide and subsequent triphenylphosphine induced cyclization. BF3-induced reaction of compounds 3a-e resulted in a rearrangement via a cyclopropyl carbinyl cation intermediate. In the case of tosylaziridine 3c bicyclic product 5, (tropane skeleton), was formed as the major product. With carbamate derivative 3a exclusive rearrangement to fluorocyloheptene 7 took place.

Place, publisher, year, edition, pages
1996. Vol. 37, no 19, 3371-3374 p.3371-3374 p.
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Natural Sciences
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URN: urn:nbn:se:uu:diva-69841DOI: 10.1016/0040-4039(96)00549-7OAI: oai:DiVA.org:uu-69841DiVA: diva2:97752
Available from: 2008-10-17 Created: 2008-10-17 Last updated: 2017-11-21Bibliographically approved

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