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Enantioselective Synthesis of Substituted Piperidines by Addition of Aryl Grignard Reagents to Pyridine N-Oxides.

Hussain, Munawar; Banchelin, Thomas Sainte-Luce; Andersson, Hans; Olsson, Roger LU and Almqvist, Fredrik (2012) In Organic Letters
Abstract
The synthesis of optically active piperidines by enantioselective addition of aryl Grignard reagents to pyridine N-oxides and lithium binolate followed by reduction is reported for the first time. The reaction results in high yields (51-94%) in combination with good ee (54-80%). Some of these products were subsequently recrystallized, affording enhanced optical purities (>99% ee).
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic Letters
publisher
The American Chemical Society
external identifiers
  • wos:000313156400015
  • pmid:23256529
  • scopus:84874037155
ISSN
1523-7052
DOI
10.1021/ol303085q
language
English
LU publication?
yes
id
16a4ab6c-c0a8-445f-9b2a-436e1a983bfd (old id 3347016)
alternative location
http://www.ncbi.nlm.nih.gov/pubmed/23256529?dopt=Abstract
date added to LUP
2013-01-02 13:30:30
date last changed
2017-09-10 04:47:08
@article{16a4ab6c-c0a8-445f-9b2a-436e1a983bfd,
  abstract     = {The synthesis of optically active piperidines by enantioselective addition of aryl Grignard reagents to pyridine N-oxides and lithium binolate followed by reduction is reported for the first time. The reaction results in high yields (51-94%) in combination with good ee (54-80%). Some of these products were subsequently recrystallized, affording enhanced optical purities (>99% ee).},
  author       = {Hussain, Munawar and Banchelin, Thomas Sainte-Luce and Andersson, Hans and Olsson, Roger and Almqvist, Fredrik},
  issn         = {1523-7052},
  language     = {eng},
  month        = {12},
  publisher    = {The American Chemical Society},
  series       = {Organic Letters},
  title        = {Enantioselective Synthesis of Substituted Piperidines by Addition of Aryl Grignard Reagents to Pyridine N-Oxides.},
  url          = {http://dx.doi.org/10.1021/ol303085q},
  year         = {2012},
}