Issue 14, 2010
From the journal:

Chemical Communications

Organocatalytic asymmetric synthesis of polyfunctionalized 3-(cyclohexenylmethyl)-indoles via a quadruple domino Friedel–Crafts-type/Michael/Michael/aldol condensation reaction†

Dieter Enders,*a   Chuan Wang,a   Meruyert Mukanovaa  and  Andreas Greba  

* Corresponding authors

a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
E-mail: enders@rwth-aachen.de
Fax: +49-241-809-2127
Tel: +49-241-809-4676

Abstract

A new organocatalytic quadruple domino Friedel–Crafts-type/Michael/Michael/aldol condensation reaction has been developed. In this one-pot multi-component process acrolein, various indoles and nitroalkenes are used as starting materials. The diphenylprolinol TMS-ether catalysis provides a straightforward and efficient entry to 3-(cyclohexenylmethyl)-indoles bearing three stereogenic centers in moderate to excellent yields (23–82%) and excellent stereoselectivities (dr = 91 ∶ 9 to >95 ∶ 5, ee = 94 to >99%).

Graphical abstract: Organocatalytic asymmetric synthesis of polyfunctionalized 3-(cyclohexenylmethyl)-indoles via a quadruple domino Friedel–Crafts-type/Michael/Michael/aldol condensation reaction

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Article information

DOI
https://doi.org/10.1039/C002839H
Article type
Communication
Submitted
10 Feb 2010
Accepted
24 Feb 2010
First published
08 Mar 2010

Chem. Commun., 2010,46, 2447-2449

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Organocatalytic asymmetric synthesis of polyfunctionalized 3-(cyclohexenylmethyl)-indoles via a quadruple domino Friedel–Crafts-type/Michael/Michael/aldol condensation reaction

D. Enders, C. Wang, M. Mukanova and A. Greb, Chem. Commun., 2010, 46, 2447 DOI: 10.1039/C002839H

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