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

Magnus Rueping; Francisco Tato; Fenja R. Schoepke

doi:10.1002/chem.200902907

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 journal › Article › peer-review

174 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 language	English (US)
Pages (from-to)	2688-2691
Number of pages	4
Journal	Chemistry - A European Journal
Volume	16
Issue number	9
DOIs	https://doi.org/10.1002/chem.200902907
State	Published - Mar 1 2010
Externally published	Yes

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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10.1002/chem.200902907

Cite this

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

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.",

keywords = "Br{\o}nsted acid, Hantzsch ester, Organocatalysis, Pyrazine, Pyridine, Transfer hydrogenation",

author = "Magnus Rueping and Francisco Tato and Schoepke, {Fenja R.}",

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).",

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doi = "10.1002/chem.200902907",

language = "English (US)",

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AU - Tato, Francisco

AU - Schoepke, Fenja R.

N1 - 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).

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N2 - (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.

AB - (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.

KW - Brønsted acid

KW - Hantzsch ester

KW - Organocatalysis

KW - Pyrazine

KW - Pyridine

KW - Transfer hydrogenation

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JO - Chemistry - A European Journal

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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