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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 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%.

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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
2020-01-13 02:26:02
@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},
}