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Diastereoselective Synthesis of Indanes and Tetralins via Intramolecular Friedel–Crafts Reaction

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Org. Lett., 2013, 15 (6), pp 1370–1373
DOI: 10.1021/ol400341p
Publication Date (Web): March 6, 2013
Copyright © 2013 American Chemical Society
niggemann@oc.rwth-aachen.de, †

These authors contributed equally.

Abstract

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An easy access to tetralin and indane skeletons has been developed using a diastereoselective intramolecular Friedel–Crafts alkylation. Treatment of diastereomeric mixtures of benzyl carbinols with a catalytic amount of Ca(NTf2)2/Bu4NPF6 yields the respective tetralin or indane in good yields with high levels of regio- and diastereoselectivity.

Supporting Information

Complete experimental details and compound characterization data, as well as copies of 1H NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 1,216 Times
Received 5 February 2013
Published online 6 March 2013
Published in print 15 March 2013
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