Reactions between Grignard reagents and heterocyclic N-oxides : Stereoselective synthesis of substituted pyridines, piperidines, and piperazines
Andersson, Hans ; Olsson, Roger LU
and Almqvist, Fredrik
(2011)
In Organic and Biomolecular Chemistry
9(2).
p.337-346
- Abstract
In this perspective we discuss the recent developments of stereoselective synthesis of substituted pyridines, piperidines, and piperazines from cheap and commercially readily available starting materials. Pyridine N-oxides and pyrazine N-oxides are reacted with alkyl, aryl, alkynyl and vinyl Grignard reagents to give a diverse set of heterocycles in high yields. Optically active substituted piperazines are obtained by an asymmetric reaction from pyrazine N-oxides using sparteine as chiral ligand. In addition, a stereoselective synthesis of dienal-oximes from the reaction between pyridine N-oxides and Grignard reagents is presented, which results in a useful intermediate for the synthesis of a diverse set of compounds.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/679f0f0e-71a6-4332-9219-87025db20c90
- author
- Andersson, Hans
; Olsson, Roger
LU
and Almqvist, Fredrik
- publishing date
- 2011-01-21
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Organic and Biomolecular Chemistry
- volume
- 9
- issue
- 2
- pages
- 10 pages
- publisher
- Royal Society of Chemistry
- external identifiers
-
- scopus:78650743607
- ISSN
- 1477-0520
- DOI
- 10.1039/c0ob00336k
- language
- English
- LU publication?
- no
- id
- 679f0f0e-71a6-4332-9219-87025db20c90
- date added to LUP
- 2019-10-02 10:09:57
- date last changed
- 2022-02-01 01:07:41
@article{679f0f0e-71a6-4332-9219-87025db20c90,
abstract = {{<p>In this perspective we discuss the recent developments of stereoselective synthesis of substituted pyridines, piperidines, and piperazines from cheap and commercially readily available starting materials. Pyridine N-oxides and pyrazine N-oxides are reacted with alkyl, aryl, alkynyl and vinyl Grignard reagents to give a diverse set of heterocycles in high yields. Optically active substituted piperazines are obtained by an asymmetric reaction from pyrazine N-oxides using sparteine as chiral ligand. In addition, a stereoselective synthesis of dienal-oximes from the reaction between pyridine N-oxides and Grignard reagents is presented, which results in a useful intermediate for the synthesis of a diverse set of compounds.</p>}},
author = {{Andersson, Hans and Olsson, Roger and Almqvist, Fredrik}},
issn = {{1477-0520}},
language = {{eng}},
month = {{01}},
number = {{2}},
pages = {{337--346}},
publisher = {{Royal Society of Chemistry}},
series = {{Organic and Biomolecular Chemistry}},
title = {{Reactions between Grignard reagents and heterocyclic N-oxides : Stereoselective synthesis of substituted pyridines, piperidines, and piperazines}},
url = {{http://dx.doi.org/10.1039/c0ob00336k}},
doi = {{10.1039/c0ob00336k}},
volume = {{9}},
year = {{2011}},
}