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

Fredrik Schlyter; Carina Eriksson; Hans-Erik Högberg; Kristina Sjödin

doi:10.1016/j.tetasy.2006.03.033

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

Fredrik Schlyter
, Carina Eriksson
, Hans-Erik Högberg
, Kristina Sjödin

Publication: Contribution to journal › Journal article › peer-review

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.

Original language	English
Pages (from-to)	1074-1080
Number of pages	7
Journal	Tetrahedron: Asymmetry
Volume	17
Issue number	7
DOIs	https://doi.org/10.1016/j.tetasy.2006.03.033
Publication status	Published - 2006

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

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.",

author = "Fredrik Schlyter and Carina Eriksson and Hans-Erik H{\"o}gberg and Kristina Sj{\"o}din",

year = "2006",

doi = "10.1016/j.tetasy.2006.03.033",

language = "English",

volume = "17",

pages = "1074--1080",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

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T1 - Synthesis of (+)- and (-)-dihydropinidine by diastereoselective dimethylzinc promoted allylation of 2-methyltetrahydropyridine-N-oxide with an allylboronic ester

AU - Schlyter, Fredrik

AU - Eriksson, Carina

AU - Högberg, Hans-Erik

AU - Sjödin, Kristina

PY - 2006

Y1 - 2006

N2 - 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.

AB - 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.

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

UR - http://www-vv.slu.se/fs/sch-pub.htm

U2 - 10.1016/j.tetasy.2006.03.033

DO - 10.1016/j.tetasy.2006.03.033

M3 - Journal article

SN - 0957-4166

VL - 17

SP - 1074

EP - 1080

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 7

ER -

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

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