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Synfacts 2010(12): 1428-1428  
DOI: 10.1055/s-0030-1258922
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular Aza-Michael Addition of Indoles

Contributor(s): Benjamin List, Ji-Woong Lee
Q. Cai, C. Zheng, S.-L. You*
Shanghai Institute of Organic Chemistry, P. R. oF China
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

Indole alkaloids are a common core structure in natural products. Herein, the authors report the enantioselective intramolecular aza-Michael additions of C2-substituted indoles 2 to N-alkylated products 3 catalyzed by phosphoric acid 1 (er up to 96.5:3.5). Various aryl enones are tolerated in the reaction and give good enantio­selectivity with high chemoselectivity. Moreover, substrates 2 can be prepared in situ by olefin cross-metathesis using catalyst 4 in the presence of phosphoric acid catalyst 1 to afford the desired products in good enantioselectivity.