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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 universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen, Avdelningen för organisk kemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen, Avdelningen för organisk kemi.
1996 (engelsk)Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 37, nr 19, s. 3371-3374s. 3371-3374Artikkel i tidsskrift (Fagfellevurdert) 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.

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1996. Vol. 37, nr 19, s. 3371-3374s. 3371-3374
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URN: urn:nbn:se:uu:diva-69841DOI: 10.1016/0040-4039(96)00549-7OAI: oai:DiVA.org:uu-69841DiVA, id: diva2:97752
Tilgjengelig fra: 2008-10-17 Laget: 2008-10-17 Sist oppdatert: 2017-11-21bibliografisk kontrollert

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