Synthesis of (+)- and (-)-dihydropinidine by diastereoselective dimethylzinc promoted allylation of 2-methyltetrahydropyridine-N-oxide with an allylboronic ester

Eriksson C, Sjodin K, Schlyter F, Hogberg HE

doi:10.1016/j.tetasy.2006.03.033

Research article - Peer-reviewed, 2006

Synthesis of (+)- and (-)-dihydropinidine by diastereoselective dimethylzinc promoted allylation of 2-methyltetrahydropyridine-N-oxide with an allylboronic ester

Eriksson C, Sjodin K, Schlyter F, Hogberg HE

Abstract

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. (c) 2006 Elsevier Ltd. All rights reserved

Published in

Tetrahedron: Asymmetry
2006, volume: 17, number: 7, pages: 1074-1080
Publisher: PERGAMON-ELSEVIER SCIENCE LTD

Authors' information

Schlyter, Fredrik

Swedish University of Agricultural Sciences, Department of Crop Science

Eriksson, Carina

Högberg, Hans-Erik

Sjödin, Kristina

UKÄ Subject classification

Landscape Architecture

Publication Identifiers

DOI: https://doi.org/10.1016/j.tetasy.2006.03.033

URI (permanent link to this page)

https://res.slu.se/id/publ/9494