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

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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%.

Detaljer

Författare
  • Hans Andersson
  • Thomas Sainte Luce Banchelin
  • Sajal Das
  • Magnus Gustafsson
  • Roger Olsson
  • Fredrik Almqvist
Externa organisationer
  • Umeå University
  • ACADIA Pharmaceuticals AB
  • Göteborgs universitet
Originalspråkengelska
Sidor (från-till)284-286
Antal sidor3
TidskriftOrganic Letters
Volym12
Utgåva nummer2
StatusPublished - 2010 jan 15
PublikationskategoriForskning
Peer review utfördJa
Externt publiceradJa