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Complete regioselective addition of grignard reagents to pyrazine N-oxides, toward an efficient enantioselective synthesis of substituted piperazines
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Acadia Pharmaceuticals AB, Medeon Science Park S-20512, Malmö, Sweden.
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2010 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 12, no 2, 284-6 p.Article in journal (Refereed) Published
Abstract [en]

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%.

Place, publisher, year, edition, pages
American Chemical Society , 2010. Vol. 12, no 2, 284-6 p.
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Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-30813DOI: 10.1021/ol902619hISI: 000273428800021PubMedID: 20000607OAI: oai:DiVA.org:umu-30813DiVA: diva2:287216
Available from: 2010-01-18 Created: 2010-01-18 Last updated: 2017-12-12Bibliographically approved

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Almqvist, Fredrik

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