The first general, efficient and highly enantioselective reduction of quinoxalines and quinoxalinones

Magnus Rueping*, Francisco Tato, Fenja R. Schoepke

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

170 Scopus citations

Abstract

(Chemical Equation Presented) Simple yet efficient: A series of diverse substituted tetrahydroquinoxalines and dihydroquinoxalinones have been synthesized for the first time in a highly enantioselective fashion (see scheme). Using this metalfree hydrogenation it is possible to isolate these products, which are of high pharmaceutical interest, in good yields and with excellent enantioselectivities in a minimal number of reaction steps.

Original languageEnglish (US)
Pages (from-to)2688-2691
Number of pages4
JournalChemistry - A European Journal
Volume16
Issue number9
DOIs
StatePublished - Mar 1 2010
Externally publishedYes

Bibliographical note

Funding Information:
ACKNOWLEDGEMENTS This paper is dedicated to the memory of Professor Alexander A. Kazakov who made a large contribution to the education of the authors. Professor Kazakov, whose work is mentioned several times here, died suddenly when this paper was in press. The authors thank S. M. Razgonyaev for preparation of the large-grain ingots used for extracting single crystals, and V. Sechovskq for helpful discussions. The work was supported by the Grant Agency of the Academy of Sciences of the Czech Republic (grant No. A-1010614) and by the Grant Agency of the Czech Republic (grant No. 202/96/0207).

Keywords

  • Brønsted acid
  • Hantzsch ester
  • Organocatalysis
  • Pyrazine
  • Pyridine
  • Transfer hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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