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Regio- and Stereoselective Alkylation of Pyridine-N-oxides : Synthesis of Substituted Piperidines and Pyridines

Barange, Deepak Kumar; Johnson, Magnus T. LU ; Cairns, Andrew G.; Olsson, Roger LU and Almqvist, Fredrik (2016) In Organic Letters 18(24). p.6228-6231
Abstract

Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic Letters
volume
18
issue
24
pages
4 pages
publisher
The American Chemical Society
external identifiers
  • scopus:85006474723
  • wos:000390180300004
ISSN
1523-7060
DOI
10.1021/acs.orglett.6b02667
language
English
LU publication?
yes
id
ef527068-00ed-4a40-a8f4-2183009c5a9a
date added to LUP
2017-01-11 13:17:48
date last changed
2017-09-18 11:35:51
@article{ef527068-00ed-4a40-a8f4-2183009c5a9a,
  abstract     = {<p>Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.</p>},
  author       = {Barange, Deepak Kumar and Johnson, Magnus T. and Cairns, Andrew G. and Olsson, Roger and Almqvist, Fredrik},
  issn         = {1523-7060},
  language     = {eng},
  month        = {12},
  number       = {24},
  pages        = {6228--6231},
  publisher    = {The American Chemical Society},
  series       = {Organic Letters},
  title        = {Regio- and Stereoselective Alkylation of Pyridine-N-oxides : Synthesis of Substituted Piperidines and Pyridines},
  url          = {http://dx.doi.org/10.1021/acs.orglett.6b02667},
  volume       = {18},
  year         = {2016},
}