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Synfacts 2008(12): 1301-1301  
DOI: 10.1055/s-0028-1083616
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Iridium-Catalyzed Allylic Substitution Reactions in Tryptamine Synthesis

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
B. P. Bondzic, A. Farwick, J. Liebich, P. Eilbracht*
Technische Universität Dortmund, Germany
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Publikationsdatum:
20. November 2008 (online)

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Significance

In this paper, the authors explored a highly diversity-oriented strategy for the synthesis of tryptamines and homologues by combination of enantioselective allylation with a tandem hydroformylation-Fischer indole synthesis. Because stereocenters next to the olefinic bond are tolerated and do not epimerize, β-branched tryptamines were obtained with high enantiomeric purities.