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Synthesis 2009(24): 4119-4124  
DOI: 10.1055/s-0029-1217069
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of 3H-Pyrrolo[1,2-a]indole-2-carbaldehydes via an Organocatalytic Domino Aza-Michael/Aldol Condensation Reaction

Dieter Enders*, Chuan Wang, Gerhard Raabe
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;
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Publikationsverlauf

Received 27 August 2009
Publikationsdatum:
22. Oktober 2009 (online)

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Abstract

A simple organocatalytic aza-Michael/aldol condensation domino reaction protocol opens an efficient and enantioselective entry to the tricyclic pyrrolo indole core, a characteristic structural unit of many bioactive natural products.

Key words

pyrrolo[1,2-a]indole - organocatalysis - domino reaction - aza-Michael reaction - asymmetric synthesis

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CCDC-737780 contains the supplementary crystallographic data for the compound 3b reported in this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.