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Chem Commun (Camb). 2014 Jan 14;50(4):445-7. doi: 10.1039/c3cc47841f.

Asymmetric synthesis of 3,4-annulated indoles through an organocatalytic cascade approach.

Chemical communications (Cambridge, England)

Lorenzo Caruana, Mariafrancesca Fochi, Mauro Comes Franchini, Silvia Ranieri, Andrea Mazzanti, Luca Bernardi

Affiliations

  1. Department of Industrial Chemistry "Toso Montanari", School of Science, University of Bologna, V. Risorgimento 4, 40136, Bologna, Italy. [email protected] [email protected].

PMID: 24252947 DOI: 10.1039/c3cc47841f

Abstract

Indoles bearing Michael acceptors at the 4-position were engaged in organocatalytic enantioselective cascade reactions with enals. Careful optimisation of the reaction parameters overcame the inherent low reactivity of these substrates, rendering 3,4-ring fused indoles in good yields, excellent enantioselectivities and as single diastereoisomers.

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