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DOI: 10.1055/s-0028-1083616
Iridium-Catalyzed Allylic Substitution Reactions in Tryptamine Synthesis
Contributor(s):Hisashi Yamamoto, Cheol Hong CheonTechnische Universität Dortmund, Germany
Application of Iridium Catalyzed Allylic Substitution Reactions in the Synthesis of Branched Tryptamines and Homologues via Tandem Hydroformylation-Fischer Indole Synthesis
Org. Biomol. Chem. 2008, 6: 3723-3731
Publication History
Publication Date:
20 November 2008 (online)
Key words
tryptamines - tandem hydroformylation-Fischer indole synthesis - iridium
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.
Comment
Recently, the Eilbracht group reported the synthesis of branched tryptamines via a tandem hydroformylatioin-Fischer indole synthesis sequence (J. Org. Chem. 2005, 70, 5528). In this paper, they extended their methodology to the preparation of enantiopure branched tryptamines combined with efficient enantioselective synthesis of the olefinic starting materials.