BF3-induced rearrangement of aziridinocyclopropanes derived from 2-phenylsulfonyl-1,3-dienes: A new approach to the tropane alkaloid skeleton
1996 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1873-3581, Vol. 37, no 19, 3371-3374 p.3371-3374 p.Article in journal (Refereed) Published
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.
IdentifiersURN: urn:nbn:se:uu:diva-69841DOI: 10.1016/0040-4039(96)00549-7OAI: oai:DiVA.org:uu-69841DiVA: diva2:97752