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Synlett 2011(9): 1243-1246  
DOI: 10.1055/s-0030-1259955
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© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of Quinolizidines and Indolizidines via a Catalytic Asymmetric Hydrogenation Cascade

Magnus Rueping*, Lukas Hubener
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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Publication History

Received 31 January 2011
Publication Date:
18 April 2011 (online)

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Abstract

A catalytic enantioselective synthesis of a new class of quinolizidines and indolizidines is presented. An asymmetric Brønsted acid catalyzed hydrogenation cascade as well as a sequential Brønsted acid/metal catalyzed hydrogenation protocol of 2-substituted quinolines yields benzofused quinolizidines and indolizidines in good yields with high diastereo- and enantioselectivities.

Key words

organocatalysis - domino reaction - amines - asymmetric reduction - Hantzsch ester

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18

Rueping, M.; Koenigs, R. M.; Borrmann, R.; Zoller, J.; Weirich, T. E.; Mayer, J. manuscript in preparation.