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Synthesis of enantiomerically pure 4-substituted pyrrolidin-3-ols via asymmetric 1,3-dipolar cycloaddition
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
2001 (English)In: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 12, no 14, p. 1977-1982Article in journal (Refereed) Published
Abstract [en]

Asymmetric 1,3-dipolar cycloadditions of chiral azomethine ylides to 3-benzyloxy-substituted alkenoylcamphorsultams are described. trans-3,4-Disubstituted pyrrolidines containing a protected hydroxyl group at C(4) of the pyrrolidine ring are obtained in high diastereomeric ratios. Such compounds can serve as chiral building blocks for the syntheses of enantiopure bioactive pyrrolidines. This is exemplified by a short synthetic route to a known glycosidase inhibitor, (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol and its enantiomer.

Place, publisher, year, edition, pages
2001. Vol. 12, no 14, p. 1977-1982
Keywords [en]
dipolar cycloaddition
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-4074DOI: 10.1016/S0957-4166(01)00367-6ISI: 000171514000006Scopus ID: 2-s2.0-0035859709Local ID: 4594OAI: oai:DiVA.org:miun-4074DiVA, id: diva2:29106
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-17Bibliographically approved

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Karlsson, StaffanHögberg, Hans-Erik

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