Complete regioselective addition of grignard reagents to pyrazine N-oxides, toward an efficient enantioselective synthesis of substituted piperazines
(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:
https://lup.lub.lu.se/record/cbaebad9-9e43-4ecc-91b1-78998ce69939
- author
- Andersson, Hans ; Banchelin, Thomas Sainte Luce ; Das, Sajal ; Gustafsson, Magnus LU ; Olsson, Roger LU and Almqvist, Fredrik
- publishing date
- 2010-01-15
- 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}}, }