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The regio- and stereoselective synthesis of trans-2,3-dihydropyridine n-oxides and piperidines

Andersson, Hans ; Gustafsson, Magnus LU ; Boström, Dan ; Olsson, Roger LU orcid and Almqvist, Fredrik (2009) In Angewandte Chemie - International Edition 48(18). p.3288-3291
Abstract

Reactivity N - Own: Pyridine N-oxides can be used for the complete regio- and stereoselective synthesis of trans-substituted piperidines. The sequential addition of Grignard reagents and aldehydes or ketones to pyridine N-oxides yields a complete regio- and stereoselective trans 2,3- addition reaction in high yields, and the substituted 2,3-dihydropyridine N-oxide can be reduced to form 2,3-trans-substituted piperidines (see scheme).

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author
; ; ; and
publishing date
type
Contribution to journal
publication status
published
subject
in
Angewandte Chemie - International Edition
volume
48
issue
18
pages
3288 - 3291
publisher
John Wiley & Sons Inc.
external identifiers
  • pmid:19322871
  • scopus:70349913580
ISSN
1433-7851
DOI
10.1002/anie.200900189
language
English
LU publication?
no
id
53c0e0ef-29ce-402f-bf6b-795df0204bfc
date added to LUP
2019-10-02 10:02:38
date last changed
2025-10-14 11:34:47
@article{53c0e0ef-29ce-402f-bf6b-795df0204bfc,
  abstract     = {{<p>Reactivity N - Own: Pyridine N-oxides can be used for the complete regio- and stereoselective synthesis of trans-substituted piperidines. The sequential addition of Grignard reagents and aldehydes or ketones to pyridine N-oxides yields a complete regio- and stereoselective trans 2,3- addition reaction in high yields, and the substituted 2,3-dihydropyridine N-oxide can be reduced to form 2,3-trans-substituted piperidines (see scheme).</p>}},
  author       = {{Andersson, Hans and Gustafsson, Magnus and Boström, Dan and Olsson, Roger and Almqvist, Fredrik}},
  issn         = {{1433-7851}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{18}},
  pages        = {{3288--3291}},
  publisher    = {{John Wiley & Sons Inc.}},
  series       = {{Angewandte Chemie - International Edition}},
  title        = {{The regio- and stereoselective synthesis of trans-2,3-dihydropyridine n-oxides and piperidines}},
  url          = {{http://dx.doi.org/10.1002/anie.200900189}},
  doi          = {{10.1002/anie.200900189}},
  volume       = {{48}},
  year         = {{2009}},
}