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Issue 10, 2012
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A detailed study of the diastereoselective catalytic hydrogenation of 6-hydroxytetrahydroisoquinoline-(3R)-carboxylic ester intermediates

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Abstract

A key step towards a highly-selective antagonist of ionotropic glutamate receptors entails the diastereoselective arene hydrogenation of an enantiopure tetrahydroisoquinoline. An extensive screen using parallel reactors was conducted and led to the discovery of several Pd/C catalysts giving high yield and improved diastereoselectivity from 75 : 25 to 95 : 5. A detailed kinetic study of the best system was performed and supports the reduction occuring in two-steps.

Graphical abstract: A detailed study of the diastereoselective catalytic hydrogenation of 6-hydroxytetrahydroisoquinoline-(3R)-carboxylic ester intermediates

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Publication details

The article was received on 19 Apr 2012, accepted on 15 May 2012 and first published on 06 Jun 2012


Article type: Paper
DOI: 10.1039/C2CY20251D
Catal. Sci. Technol., 2012,2, 2077-2082

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    A detailed study of the diastereoselective catalytic hydrogenation of 6-hydroxytetrahydroisoquinoline-(3R)-carboxylic ester intermediates

    L. Lefort, N. Sereinig, H. Straatman, D. J. Ager, J. G. de Vries, J. A. Werner, R. B. Scherer, T. D. Maloney, M. D. Argentine, K. A. Sullivan and J. W. Fennell, Catal. Sci. Technol., 2012, 2, 2077
    DOI: 10.1039/C2CY20251D

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