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Synfacts 2011(12): 1362-1362  
DOI: 10.1055/s-0031-1289378
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Morpholine-Catalyzed C3 Alkenylation of Indoles with Enals

Contributor(s): Benjamin List, Ilija Čorić
S.-K. Xiang, B. Zhang, L.-H. Zhang, Y. Cui, N. Jiao*
Peking University, Beijing and East China Normal University, Shanghai, P. R. of China
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

The first organocatalytic C3 alken­ylation of unprotected indoles 2 with α,β-unsaturated aldehydes 3 has been reported. Morpholine ­trifluoroacetic acid salt was identified as an efficient catalyst in this oxidative dehydrogenative reaction. A variety of indoles 2 proved to be compatible substrates, and both α- and β-substituted enals are tolerated. Simplicity and practicality are attractive advantages of this reaction compared to metal-based systems. It is important to note that the oxidant DDQ was added after the initial formation of intermediate 5.