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Synlett 2010(6): 852-865  
DOI: 10.1055/s-0029-1219528
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Thieme Chemistry Journal Awardees - Where Are They Now? Asymmetric Brønsted Acid Catalyzed Transfer Hydrogenations

Magnus Rueping*, Erli Sugiono, Fenja R. Schoepke
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092665; e-Mail: Magnus.Rueping@rwth-aachen.de;
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Publikationsverlauf

Received 12 November 2009
Publikationsdatum:
18. Februar 2010 (online)

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Abstract

Asymmetric hydrogenations are of great importance in the synthesis of optically active amines. This account highlights the development of the first metal-free transfer hydrogenation that is both highly enantioselective and inspired by nature’s dehydrogen­ase. Further focus is given to the extension of this bioinspired process to provide a variety of valuable, biologically active products and natural products under mild reaction conditions.

1 Introduction

2 Nature’s Reductions: Dehydrogenases as a Role Model

3 Brønsted Acid catalyzed Transfer Hydrogenation of Ketimines

4 Asymmetric Organocatalytic Reduction of Quinolines

5 Asymmetric Organocatalytic Reduction of N-Heterocycles

5.1 Asymmetric Brønsted Acid Catalyzed Hydrogenation of ­Indoles

5.2 Asymmetric Brønsted Acid Catalyzed Hydrogenation of Benzoxazines, Benzthiazines, Benzoxazinones, Quinoxalines, Quinoxalinones and Benzodiazepinones

6 Asymmetric Organocatalytic Reduction of Pyridines

7 Asymmetric Organocatalytic Reductions in Cascade ­Sequences

8 Conclusion

Key words

binol phosphate - Brønsted acid - Hantzsch ester - transfer hydrogenation - organocatalysis - asymmetric reduction

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Rueping, M.; Stöckel, M.; Theissmann, T., manuscript submitted for publication.

33

Rueping, M.; Brinkmann, C.; Antonchick, A. P. manuscript submitted for publication.

37

Rueping, M.; Tato, F.; Schoepke, F. R. manuscript submitted for publication.

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Rueping, M.; Merino, E.; Koenigs, R. M. manuscript in preparation.