Synthesis of (+)- and (−)-dihydropinidine by diastereoselective dimethylzinc promoted allylation of 2-methyltetrahydropyridine-N-oxide with an allylboronic ester
2006 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, no 7, 1074-1080 p.Article in journal (Refereed) Published
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.
piperidine alkaloid content, asymmetric-synthesis, 2, 6-disubstituted piperidines, enantioselective synthesis, spruce, pine, reduction, route, (2s, 6r)-dihydropinidine, dihydropinidine
IdentifiersURN: urn:nbn:se:kth:diva-5601DOI: 10.1016/j.tetasy.2006.03.033ISI: 000238279900011OAI: oai:DiVA.org:kth-5601DiVA: diva2:10019
QC 20110124. Uppdaterad från submitted till published(20110124)2006-04-112006-04-112011-01-24Bibliographically approved