Skip to main content

Lund University Publications

LUND UNIVERSITY LIBRARIES

Complete regioselective addition of grignard reagents to pyrazine N-oxides, toward an efficient enantioselective synthesis of substituted piperazines

Andersson, Hans ; Banchelin, Thomas Sainte Luce ; Das, Sajal ; Gustafsson, Magnus LU ; Olsson, Roger LU orcid and Almqvist, Fredrik (2010) In Organic Letters 12(2). p.284-286
Abstract

(Figure presented) A conceptually new one-pot strategy for the synthesis of protected substituted piperazines via the addition of Grignard reagents to pyrazine N-oxides is presented. This strategy is high yielding (33-91% over three steps), step-efficient, and fast. The synthesized N,N-diprotected piperazines are convenient to handle and allow for orthogonal deprotection at either nitrogen for selective transformations. In addition, this Is a synthetic route to enantiomerically enriched piperazines by using a combination of phenyl magnesium chloride and (-)-sparteine, which resulted In enantiomeric excesses up to 83%.

Please use this url to cite or link to this publication:
author
; ; ; ; and
publishing date
type
Contribution to journal
publication status
published
in
Organic Letters
volume
12
issue
2
pages
3 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:20000607
  • scopus:74949116077
ISSN
1523-7060
DOI
10.1021/ol902619h
language
English
LU publication?
no
id
cbaebad9-9e43-4ecc-91b1-78998ce69939
date added to LUP
2019-10-02 09:41:01
date last changed
2024-01-01 21:22:17
@article{cbaebad9-9e43-4ecc-91b1-78998ce69939,
  abstract     = {{<p>(Figure presented) A conceptually new one-pot strategy for the synthesis of protected substituted piperazines via the addition of Grignard reagents to pyrazine N-oxides is presented. This strategy is high yielding (33-91% over three steps), step-efficient, and fast. The synthesized N,N-diprotected piperazines are convenient to handle and allow for orthogonal deprotection at either nitrogen for selective transformations. In addition, this Is a synthetic route to enantiomerically enriched piperazines by using a combination of phenyl magnesium chloride and (-)-sparteine, which resulted In enantiomeric excesses up to 83%.</p>}},
  author       = {{Andersson, Hans and Banchelin, Thomas Sainte Luce and Das, Sajal and Gustafsson, Magnus and Olsson, Roger and Almqvist, Fredrik}},
  issn         = {{1523-7060}},
  language     = {{eng}},
  month        = {{01}},
  number       = {{2}},
  pages        = {{284--286}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Organic Letters}},
  title        = {{Complete regioselective addition of grignard reagents to pyrazine N-oxides, toward an efficient enantioselective synthesis of substituted piperazines}},
  url          = {{http://dx.doi.org/10.1021/ol902619h}},
  doi          = {{10.1021/ol902619h}},
  volume       = {{12}},
  year         = {{2010}},
}