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Synthesis of (+)- and (-)-dihydropinidine by diastereoselective dimethylzinc promoted allylation of 2-methyltetrahydropyridine-N-oxide with allylboronic ester.
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.
Swedish University of Agricultural Sciences, Alnarp.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
2006 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, no 7, 1074-1080 p.Article in journal (Refereed) Published
Abstract [en]

The enantiomers of the naturally occurring alkaloid dihydropinidine 1, potential antifeedants against the pine weevil, Hylobius abietis, were prepared by diastereoselective, dimethylzinc mediated addition of pinacolyl 2-propenylboronate 14 to nitrones (R)- and (S)-2-methyl tetrahydropyridine-N-oxide 3, prepared from d- and l-alanine, respectively.

Place, publisher, year, edition, pages
2006. Vol. 17, no 7, 1074-1080 p.
Keyword [en]
dihydropininidine, dimethylzinc, enantioselective synthesis
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-3906DOI: 10.1016/j.tetasy.2006.03.033ISI: 000238279900011Scopus ID: 2-s2.0-33646508340Local ID: 4268OAI: oai:DiVA.org:miun-3906DiVA: diva2:28938
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-09-28Bibliographically approved

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Eriksson, CarinaSjödin, KristinaHögberg, Hans-Erik
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