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Synfacts 2009(10): 1161-1161  
DOI: 10.1055/s-0029-1217942
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective N-Acyliminium Cyclization Cascade

Contributor(s): Benjamin List, Frank Lay
M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon*
The University of Manchester, University of Oxford, Pfizer Global Research & Development, Sandwich and UCB, Slough, UK
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

The authors developed an enantio-selective Brønsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form complex heterocycles. Moderate to high yields and high enantioselectivities have been achieved with chiral phosphoric acid catalysts. With doubly substituted enol lactones just one of the possible two diastereomers was observed.